Methyl 3-{2-[(acetyloxy)methyl]-4-[(tert-butoxycarbonyl)amino]-3-methylphenyl}-2-{[(benzyloxy)carbonyl]amino}prop-2-enoate → 3-(2-Acetoxymethyl-4-tert-butoxycarbonylamino-3-methyl-phenyl)-2-(R)-benzyloxycarbonylamino-propionic acid methyl ester

HRID 132156Notes

Reaction equation

HRID 132156 reaction equation
[CH3:1][O:2][C:3](=[O:37])[C:4]([NH:26][C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28])=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[C:8]([CH3:20])[C:7]=1[CH2:21][O:22][C:23](=[O:25])[CH3:24].C(OC(=O)[C@H](C(COC(=O)C)C1C=CC(NC(OC(C)(C)C)=O)=C(C)C=1)CC(OCC)=O)C>CO.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:37])[C@H:4]([NH:26][C:27]([O:29][CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)=[O:28])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:17])[CH3:18])=[O:14])=[C:8]([CH3:20])[C:7]=1[CH2:21][O:22][C:23](=[O:25])[CH3:24]

Participants

5

Reactant 2

HCID 53415138Methyl 3-{2-[(acetyloxy)methyl]-4-[(tert-butoxycarbonyl)amino]-3-methylphenyl}-2-{[(benzyloxy)carbonyl]amino}prop-2-enoateHCID 673188002-(S)-(acetoxymethyl-4-tert-butoxycarbonylamino-3-methyl-benzyl)-succinic acid diethyl ester

Product 1

HCID 597318653-(2-Acetoxymethyl-4-tert-butoxycarbonylamino-3-methyl-phenyl)-2-(R)-benzyloxycarbonylamino-propionic acid methyl esterYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-(2-acetoxymethyl-4-tert-butoxycarbonylamino-3-methyl-phenyl)-2-benzyloxycarbonylamino-acrylic acid methyl ester (2.51 g, 4.9 mmol) in methanol (50 mL) and ethyl acetate (15 mL) was reacted in a manner similar to the preparation of 2-(S)-(acetoxymethyl-4-tert-butoxycarbonylamino-3-methyl-benzyl)-succinic acid diethyl ester. Title compound was obtained as an off-white solid in 97% yield. 1H NMR (300 MHz, CDCl3): δ=7.66 (d, J=7.9, 1H), 7.31 (m, 5H), 6.99 (d, J=8.5, 1H), 6.21 (s, 1H), 5.31 (d, J=7.6, 1H), 5.17 (d, J=3.7, 2H), 5.04 (d, J=5.80, 2H), 4.56 (m, 1H), 3.71 (s, 3H), 3.23 (dd, J1=5.80, J2=14.7, 1H), 3.07 (dd, J1=7.8, J2=14.2, 1H), 2.21 (s, 3H), 2.00 (s, 3H), 1.50 (s, 9H). MS m/e (M−H)−=513.0.

Sources & evidence

ORD record
ord-108a8deda6dc4c76b22081b4b6d74791
Source dataset
uspto-grants-2008_06
Patent number
US07384930B2

Reaction notes

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