organic compounds
Methyl (2R)-2-benzamido-2-{[(1R)-2-methoxy-2-oxo-1-phenylethyl]amino}acetate
aFormation Doctorale Molécules Bioactives, Santé et Biotechnologies, Centre détudes Doctorales Sciences et Technologies, LCO, Faculté des Sciences Dhar El Marhaz, Fès, Morocco, bLaboratoire de Chimie Organique, Faculté des Sciences Dhar el Mahraz, Université Sidi Mohammed Ben Abdellah, Fès, Morocco, and cLaboratoire de Chimie des Matériaux et Biotechnologie des Produits Naturels, E.Ma.Me.P.S., Université Moulay Ismail, Faculté des Sciences, Meknès, Morocco
*Correspondence e-mail: anouar.alami@usmba.ac.ma
In the title compound, C19H20N2O5, the dihedral angle between the phenyl rings is 58.85 (8)°, while that between the planes of the methyl acetate groups is 88.30 (8)°. The is also influenced by the presence of an intramolecular N—H⋯O hydrogen bond. In the crystal, N—H⋯O hydrogen bonds link the molecules, forming chains propagating along the a-axis direction.
CCDC reference: 1566970
Structure description
The synthesis of new α-AAs (α-aminoacetates) and their is of international interest because of their extensive applications in enzymology, medicine, pharmacology and industry (Leite et al., 2006; Mikołajczyk, 2005; Joly et al., 2004). Our strategy used nucleophilic substitution of the N-protected methyl α-azido glycinate with 2-amino-2-phenylacetate in methylene chloride, in the presence of triethylamine as a base (Boukallaba et al., 2006) to produce the title compound in good yield.
In the title molecule (Fig. 1), the dihedral angles between the phenyl rings and those between the planes of the methyl acetate groups are 58.85 (8) and 88.30 (8)° respectively. The twisted conformation of the molecule is also influenced by the presence of an intramolecular N—H⋯O hydrogen bond (Table 1). In the crystal, N—H⋯O and C—H⋯O hydrogen bonds (Table 1, Fig. 2) link the molecules into chains propagating along the a-axis direction.
Synthesis and crystallization
To a stirred solution of methyl 2-amino-2-phenylacetate (2 mmol) and triethylamine (4 mmol) in 10 ml of dry methylene chloride, N-benzoylated methyl α-azidoglycinate (2.6 mmol) was added. The mixture was stirred at 0°C for 1 h then at room temperature for 16 h. The resulting solution was washed with citric acid (15%), then with a of sodium bicarbonate (NaHCO3). Solvents were removed and colourless single crystals of the title compound were obtained by recrystallization from ether (yield = 86%; m.p = 126–128°C.).
1H NMR (300.13 MHz; CDCl3, δH p.p.m.): 3.3 (e, 1H, NH–CH–Ph); 3.51 (s, 3H, –OCH3); 3.78 (s, 3H, –OCH3); 4.65 (s, 1H, NH–CH–Ph); 5.52 (d, 1H, N–CH–N, J = 8.4 Hz); 6.75 (d, 1H, NHBz, J = 8.4 Hz); 7.28–7.82 (m, 10Harom).
13C NMR (75.47 MHz; CDCl3, δC p.p.m.): 52.44 (1C, OCH3); 52.88 (1C, OCH3); 61.97 (1C, NH–CH—Ph); 63.62 (1C, N–CH—N); 127.13–137.48 (10C, Carom); 167.14, 170.14 and 173.63 (3C, CO).
Elemental Analysis: Calculated for C19H20N2O5 (%): C, 64.04; H, 5.66; N, 7.86; Found (%): C 63.84, H 5.67, N 7.89. MS ESI m/z (%) = 356.49.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1566970
https://doi.org/10.1107/S2414314617011555/sj4129sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617011555/sj4129Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617011555/sj4129Isup3.cml
Data collection: APEX2 (Bruker, 2005); cell
SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).C19H20N2O5 | F(000) = 752 |
Mr = 356.37 | Dx = 1.343 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 365 reflections |
a = 9.3432 (6) Å | θ = 1.6–25.2° |
b = 10.4314 (8) Å | µ = 0.10 mm−1 |
c = 18.0901 (14) Å | T = 173 K |
V = 1763.1 (2) Å3 | Prism, colourless |
Z = 4 | 0.35 × 0.16 × 0.14 mm |
Bruker APEXII CCD diffractometer | 3455 independent reflections |
Radiation source: fine-focus sealed tube | 3246 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
φ and ω scan | θmax = 26.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −11→7 |
Tmin = 0.967, Tmax = 0.986 | k = −12→12 |
28362 measured reflections | l = −22→22 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.027 | w = 1/[σ2(Fo2) + (0.0234P)2 + 0.3377P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.065 | (Δ/σ)max = 0.001 |
S = 1.04 | Δρmax = 0.14 e Å−3 |
3455 reflections | Δρmin = −0.13 e Å−3 |
246 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
2 restraints | Extinction coefficient: 0.0073 (8) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 1822 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.3 (8) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C14 | 0.12279 (14) | 0.23661 (11) | 0.98202 (7) | 0.0305 (3) | |
H14 | 0.2102 | 0.2580 | 0.9526 | 0.037* | |
N1 | 0.16831 (11) | 0.14782 (10) | 1.03988 (6) | 0.0315 (2) | |
O3 | 0.15911 (11) | 0.40644 (9) | 1.06499 (6) | 0.0464 (3) | |
O1 | −0.04242 (10) | 0.16104 (10) | 1.09856 (6) | 0.0456 (3) | |
O2 | −0.03638 (11) | 0.41900 (9) | 0.99493 (6) | 0.0475 (3) | |
C15 | 0.06822 (15) | 0.08188 (12) | 0.88463 (7) | 0.0359 (3) | |
H15 | 0.1676 | 0.1036 | 0.8684 | 0.043* | |
N2 | 0.01902 (12) | 0.18778 (10) | 0.93039 (6) | 0.0321 (2) | |
C12 | 0.12463 (14) | 0.00585 (12) | 1.14380 (7) | 0.0330 (3) | |
C18 | 0.06847 (13) | 0.36261 (11) | 1.01468 (7) | 0.0323 (3) | |
C13 | 0.07640 (13) | 0.11150 (12) | 1.09329 (7) | 0.0322 (3) | |
C1 | −0.12382 (16) | 0.15859 (14) | 0.79537 (8) | 0.0452 (3) | |
H1 | −0.1444 | 0.2276 | 0.8279 | 0.054* | |
C6 | −0.02209 (14) | 0.06888 (13) | 0.81452 (7) | 0.0353 (3) | |
C9 | 0.19247 (18) | −0.19864 (15) | 1.23588 (9) | 0.0493 (4) | |
H9 | 0.2146 | −0.2693 | 1.2669 | 0.059* | |
O5 | −0.04305 (14) | −0.07267 (10) | 0.96120 (7) | 0.0620 (3) | |
C8 | 0.27280 (17) | −0.17514 (15) | 1.17398 (9) | 0.0479 (4) | |
H8 | 0.3519 | −0.2288 | 1.1627 | 0.057* | |
C19 | 0.1260 (2) | 0.53040 (15) | 1.09662 (10) | 0.0572 (4) | |
H19A | 0.1460 | 0.5977 | 1.0602 | 0.086* | |
H19B | 0.1851 | 0.5443 | 1.1407 | 0.086* | |
H19C | 0.0246 | 0.5332 | 1.1104 | 0.086* | |
C7 | 0.23931 (16) | −0.07355 (13) | 1.12783 (8) | 0.0423 (3) | |
H7 | 0.2954 | −0.0582 | 1.0849 | 0.051* | |
C4 | −0.0684 (2) | −0.04241 (16) | 0.70022 (9) | 0.0571 (4) | |
H4 | −0.0492 | −0.1120 | 0.6678 | 0.069* | |
C5 | 0.00429 (18) | −0.03273 (15) | 0.76647 (8) | 0.0474 (4) | |
H5 | 0.0730 | −0.0960 | 0.7794 | 0.057* | |
C11 | 0.04614 (19) | −0.01734 (17) | 1.20718 (9) | 0.0560 (4) | |
H11 | −0.0316 | 0.0373 | 1.2196 | 0.067* | |
C16 | 0.07709 (18) | −0.04722 (14) | 0.92455 (8) | 0.0471 (4) | |
O4 | 0.17846 (16) | −0.11697 (13) | 0.92196 (8) | 0.0816 (4) | |
C3 | −0.1684 (2) | 0.04823 (18) | 0.68102 (9) | 0.0619 (5) | |
H3 | −0.2179 | 0.0418 | 0.6353 | 0.074* | |
C10 | 0.0801 (2) | −0.11964 (19) | 1.25270 (9) | 0.0657 (5) | |
H10 | 0.0250 | −0.1351 | 1.2959 | 0.079* | |
C2 | −0.1965 (2) | 0.14844 (17) | 0.72849 (9) | 0.0592 (4) | |
H2 | −0.2660 | 0.2110 | 0.7155 | 0.071* | |
C17 | −0.0486 (3) | −0.19393 (18) | 1.00059 (13) | 0.0933 (8) | |
H17A | −0.0225 | −0.2637 | 0.9669 | 0.140* | |
H17B | −0.1458 | −0.2081 | 1.0193 | 0.140* | |
H17C | 0.0186 | −0.1918 | 1.0421 | 0.140* | |
H1N | 0.2540 (14) | 0.1193 (14) | 1.0386 (8) | 0.039 (4)* | |
H2N | −0.0591 (14) | 0.1679 (13) | 0.9516 (7) | 0.033 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C14 | 0.0284 (6) | 0.0311 (6) | 0.0321 (6) | −0.0018 (5) | −0.0005 (5) | 0.0026 (5) |
N1 | 0.0270 (5) | 0.0325 (5) | 0.0352 (5) | 0.0043 (4) | −0.0002 (5) | 0.0039 (4) |
O3 | 0.0447 (5) | 0.0364 (5) | 0.0581 (6) | 0.0044 (4) | −0.0181 (5) | −0.0123 (5) |
O1 | 0.0363 (5) | 0.0549 (6) | 0.0454 (5) | 0.0140 (5) | 0.0072 (4) | 0.0097 (5) |
O2 | 0.0412 (6) | 0.0406 (5) | 0.0607 (6) | 0.0089 (4) | −0.0159 (5) | −0.0052 (5) |
C15 | 0.0341 (6) | 0.0374 (7) | 0.0362 (7) | −0.0007 (6) | 0.0017 (5) | −0.0037 (5) |
N2 | 0.0307 (5) | 0.0324 (5) | 0.0332 (5) | −0.0013 (4) | −0.0016 (5) | −0.0005 (4) |
C12 | 0.0340 (6) | 0.0337 (6) | 0.0314 (6) | −0.0010 (5) | −0.0040 (5) | 0.0003 (5) |
C18 | 0.0311 (6) | 0.0305 (6) | 0.0351 (6) | −0.0020 (5) | −0.0040 (5) | 0.0042 (5) |
C13 | 0.0322 (6) | 0.0333 (6) | 0.0310 (6) | 0.0022 (5) | −0.0010 (5) | −0.0018 (5) |
C1 | 0.0494 (8) | 0.0441 (8) | 0.0421 (7) | −0.0024 (7) | −0.0045 (7) | −0.0009 (6) |
C6 | 0.0383 (7) | 0.0365 (7) | 0.0310 (6) | −0.0076 (5) | 0.0033 (5) | 0.0012 (5) |
C9 | 0.0577 (9) | 0.0423 (8) | 0.0479 (8) | −0.0024 (7) | −0.0112 (7) | 0.0134 (7) |
O5 | 0.0676 (8) | 0.0449 (6) | 0.0736 (8) | −0.0110 (6) | −0.0148 (6) | 0.0246 (6) |
C8 | 0.0477 (8) | 0.0397 (7) | 0.0562 (9) | 0.0076 (7) | −0.0043 (7) | 0.0055 (7) |
C19 | 0.0653 (10) | 0.0380 (8) | 0.0681 (10) | 0.0046 (7) | −0.0147 (9) | −0.0170 (7) |
C7 | 0.0429 (8) | 0.0412 (7) | 0.0427 (7) | 0.0053 (6) | 0.0041 (6) | 0.0062 (6) |
C4 | 0.0746 (11) | 0.0543 (9) | 0.0426 (8) | −0.0127 (9) | −0.0008 (8) | −0.0113 (7) |
C5 | 0.0570 (9) | 0.0446 (8) | 0.0407 (8) | −0.0036 (7) | 0.0012 (7) | −0.0050 (7) |
C11 | 0.0566 (10) | 0.0626 (10) | 0.0487 (8) | 0.0169 (8) | 0.0150 (8) | 0.0159 (8) |
C16 | 0.0599 (9) | 0.0377 (7) | 0.0436 (8) | 0.0078 (7) | −0.0176 (7) | −0.0074 (6) |
O4 | 0.0964 (10) | 0.0652 (8) | 0.0831 (9) | 0.0450 (8) | −0.0142 (8) | −0.0072 (7) |
C3 | 0.0760 (12) | 0.0700 (11) | 0.0397 (8) | −0.0191 (10) | −0.0167 (8) | 0.0003 (8) |
C10 | 0.0731 (12) | 0.0746 (12) | 0.0494 (9) | 0.0129 (10) | 0.0160 (9) | 0.0265 (9) |
C2 | 0.0636 (10) | 0.0595 (10) | 0.0546 (10) | −0.0007 (9) | −0.0191 (8) | 0.0069 (8) |
C17 | 0.139 (2) | 0.0537 (11) | 0.0873 (14) | −0.0394 (13) | −0.0489 (15) | 0.0349 (10) |
C14—N2 | 1.4395 (16) | C9—H9 | 0.9500 |
C14—N1 | 1.4610 (16) | O5—C16 | 1.331 (2) |
C14—C18 | 1.5277 (17) | O5—C17 | 1.4527 (19) |
C14—H14 | 1.0000 | C8—C7 | 1.385 (2) |
N1—C13 | 1.3469 (17) | C8—H8 | 0.9500 |
N1—H1N | 0.855 (13) | C19—H19A | 0.9800 |
O3—C18 | 1.3246 (15) | C19—H19B | 0.9800 |
O3—C19 | 1.4474 (17) | C19—H19C | 0.9800 |
O1—C13 | 1.2282 (15) | C7—H7 | 0.9500 |
O2—C18 | 1.1973 (15) | C4—C3 | 1.374 (3) |
C15—N2 | 1.4549 (16) | C4—C5 | 1.381 (2) |
C15—C6 | 1.5294 (18) | C4—H4 | 0.9500 |
C15—C16 | 1.530 (2) | C5—H5 | 0.9500 |
C15—H15 | 1.0000 | C11—C10 | 1.385 (2) |
N2—H2N | 0.850 (12) | C11—H11 | 0.9500 |
C12—C11 | 1.382 (2) | C16—O4 | 1.1952 (19) |
C12—C7 | 1.3848 (19) | C3—C2 | 1.378 (3) |
C12—C13 | 1.5009 (17) | C3—H3 | 0.9500 |
C1—C6 | 1.378 (2) | C10—H10 | 0.9500 |
C1—C2 | 1.392 (2) | C2—H2 | 0.9500 |
C1—H1 | 0.9500 | C17—H17A | 0.9800 |
C6—C5 | 1.393 (2) | C17—H17B | 0.9800 |
C9—C8 | 1.370 (2) | C17—H17C | 0.9800 |
C9—C10 | 1.369 (2) | ||
N2—C14—N1 | 115.89 (10) | C9—C8—H8 | 119.8 |
N2—C14—C18 | 109.37 (10) | C7—C8—H8 | 119.8 |
N1—C14—C18 | 111.41 (10) | O3—C19—H19A | 109.5 |
N2—C14—H14 | 106.5 | O3—C19—H19B | 109.5 |
N1—C14—H14 | 106.5 | H19A—C19—H19B | 109.5 |
C18—C14—H14 | 106.5 | O3—C19—H19C | 109.5 |
C13—N1—C14 | 120.44 (11) | H19A—C19—H19C | 109.5 |
C13—N1—H1N | 121.3 (10) | H19B—C19—H19C | 109.5 |
C14—N1—H1N | 118.2 (10) | C12—C7—C8 | 120.44 (14) |
C18—O3—C19 | 116.33 (11) | C12—C7—H7 | 119.8 |
N2—C15—C6 | 111.39 (11) | C8—C7—H7 | 119.8 |
N2—C15—C16 | 114.64 (11) | C3—C4—C5 | 120.22 (16) |
C6—C15—C16 | 110.07 (11) | C3—C4—H4 | 119.9 |
N2—C15—H15 | 106.8 | C5—C4—H4 | 119.9 |
C6—C15—H15 | 106.8 | C4—C5—C6 | 120.67 (15) |
C16—C15—H15 | 106.8 | C4—C5—H5 | 119.7 |
C14—N2—C15 | 115.15 (10) | C6—C5—H5 | 119.7 |
C14—N2—H2N | 111.8 (9) | C12—C11—C10 | 120.44 (15) |
C15—N2—H2N | 110.0 (10) | C12—C11—H11 | 119.8 |
C11—C12—C7 | 118.61 (13) | C10—C11—H11 | 119.8 |
C11—C12—C13 | 118.31 (12) | O4—C16—O5 | 124.52 (15) |
C7—C12—C13 | 122.99 (12) | O4—C16—C15 | 124.07 (16) |
O2—C18—O3 | 123.96 (12) | O5—C16—C15 | 111.41 (12) |
O2—C18—C14 | 125.39 (12) | C4—C3—C2 | 119.61 (15) |
O3—C18—C14 | 110.51 (10) | C4—C3—H3 | 120.2 |
O1—C13—N1 | 120.90 (12) | C2—C3—H3 | 120.2 |
O1—C13—C12 | 122.21 (12) | C9—C10—C11 | 120.49 (15) |
N1—C13—C12 | 116.86 (11) | C9—C10—H10 | 119.8 |
C6—C1—C2 | 120.23 (15) | C11—C10—H10 | 119.8 |
C6—C1—H1 | 119.9 | C3—C2—C1 | 120.43 (16) |
C2—C1—H1 | 119.9 | C3—C2—H2 | 119.8 |
C1—C6—C5 | 118.82 (13) | C1—C2—H2 | 119.8 |
C1—C6—C15 | 121.92 (12) | O5—C17—H17A | 109.5 |
C5—C6—C15 | 119.17 (12) | O5—C17—H17B | 109.5 |
C8—C9—C10 | 119.61 (14) | H17A—C17—H17B | 109.5 |
C8—C9—H9 | 120.2 | O5—C17—H17C | 109.5 |
C10—C9—H9 | 120.2 | H17A—C17—H17C | 109.5 |
C16—O5—C17 | 116.64 (16) | H17B—C17—H17C | 109.5 |
C9—C8—C7 | 120.38 (15) | ||
N2—C14—N1—C13 | −68.46 (15) | N2—C15—C6—C5 | −175.99 (12) |
C18—C14—N1—C13 | 57.43 (15) | C16—C15—C6—C5 | −47.69 (17) |
N1—C14—N2—C15 | −64.44 (15) | C10—C9—C8—C7 | −1.2 (2) |
C18—C14—N2—C15 | 168.63 (10) | C11—C12—C7—C8 | 1.0 (2) |
C6—C15—N2—C14 | −158.86 (11) | C13—C12—C7—C8 | −175.46 (13) |
C16—C15—N2—C14 | 75.32 (15) | C9—C8—C7—C12 | 0.3 (2) |
C19—O3—C18—O2 | −0.1 (2) | C3—C4—C5—C6 | −0.3 (2) |
C19—O3—C18—C14 | 175.61 (13) | C1—C6—C5—C4 | 1.1 (2) |
N2—C14—C18—O2 | −7.24 (17) | C15—C6—C5—C4 | −175.50 (14) |
N1—C14—C18—O2 | −136.67 (13) | C7—C12—C11—C10 | −1.4 (2) |
N2—C14—C18—O3 | 177.07 (11) | C13—C12—C11—C10 | 175.25 (16) |
N1—C14—C18—O3 | 47.65 (14) | C17—O5—C16—O4 | 0.2 (2) |
C14—N1—C13—O1 | −6.90 (19) | C17—O5—C16—C15 | 179.10 (13) |
C14—N1—C13—C12 | 171.27 (10) | N2—C15—C16—O4 | −131.74 (15) |
C11—C12—C13—O1 | −13.9 (2) | C6—C15—C16—O4 | 101.76 (17) |
C7—C12—C13—O1 | 162.54 (13) | N2—C15—C16—O5 | 49.39 (16) |
C11—C12—C13—N1 | 167.94 (13) | C6—C15—C16—O5 | −77.11 (14) |
C7—C12—C13—N1 | −15.60 (19) | C5—C4—C3—C2 | −0.4 (3) |
C2—C1—C6—C5 | −1.2 (2) | C8—C9—C10—C11 | 0.8 (3) |
C2—C1—C6—C15 | 175.29 (14) | C12—C11—C10—C9 | 0.5 (3) |
N2—C15—C6—C1 | 7.55 (18) | C4—C3—C2—C1 | 0.3 (3) |
C16—C15—C6—C1 | 135.86 (14) | C6—C1—C2—C3 | 0.5 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2i | 0.85 (1) | 2.09 (1) | 2.9147 (15) | 162 (1) |
N2—H2N···O5 | 0.85 (1) | 2.52 (1) | 2.8334 (15) | 103 (1) |
C1—H1···N2 | 0.95 | 2.44 | 2.8000 (18) | 102 |
C7—H7···O2i | 0.95 | 2.58 | 3.4530 (18) | 153 |
Symmetry code: (i) x+1/2, −y+1/2, −z+2. |
References
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