(S)-benzyl 2-amino-3-(benzyloxy)propanoate → N-(2-acetylthiomethyl-1-oxo-3-phenylbutyl)-O-benzylserine benzyl ester

HRID 2392954Notes

Reaction equation

HRID 2392954 reaction equation
[C:1]([S:4][CH2:5][CH:6]([CH:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:11])[C:7]([OH:9])=O)(=[O:3])[CH3:2].[CH2:18]([O:25][C:26](=[O:38])[C@H:27]([CH2:29][O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[NH2:28])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[CH2:18]([O:25][C:26](=[O:38])[C@H:27]([CH2:29][O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[NH:28][C:7](=[O:9])[CH:6]([CH2:5][S:4][C:1](=[O:3])[CH3:2])[CH:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:11])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 2756658(S)-benzyl 2-amino-3-(benzyloxy)propanoateHCID 100607782-Acetylthiomethyl-3-phenylbutanoic acid

Product 1

HCID 11756403N-(2-acetylthiomethyl-1-oxo-3-phenylbutyl)-O-benzylserine benzyl esterYield 62%

Procedure

Using the procedure described in Example 60, starting with 2-acetylthiomethyl-3-phenylbutanoic acid and O-benzylserine benzyl ester, and after purification by chromatography, eluting with a hexane/ethyl acetate (8:2 by volume) mixture, N-(2-acetylthiomethyl-1-oxo-3-phenylbutyl)-O-benzylserine benzyl ester is obtained in a 62% yield, the characteristics of which are as follows: Rf =0.16 [hexane/ethyl acetate (8:2 by volume)].

Workup

  1. customafter purification by chromatography
  2. washeluting with a hexane/ethyl acetate (8:2 by volume) mixture

Sources & evidence

ORD record
ord-5d27161d4875431c8ed14ac8ead96637
Source dataset
uspto-grants-1998_09
Patent number
US05801274

Reaction notes

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