benzyl (2S)-2-aminopropanoate → N-[3-acetylthio-2-(1-indanyl)-1-oxopropyl)alanine benzyl ester

HRID 233375Notes

Reaction equation

HRID 233375 reaction equation
[C:1]([S:4][CH2:5][CH:6]([CH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11]1)[C:7]([OH:9])=O)(=[O:3])[CH3:2].[CH2:19]([O:26][C:27](=[O:31])[C@H:28]([CH3:30])[NH2:29])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH2:19]([O:26][C:27](=[O:31])[C@H:28]([CH3:30])[NH:29][C:7](=[O:9])[CH:6]([CH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11]1)[CH2:5][S:4][C:1](=[O:3])[CH3:2])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 726858benzyl (2S)-2-aminopropanoateHCID 187938683-Acetylthio-2-(1-indanyl)propanoic acid

Product 1

HCID 53659209N-[3-acetylthio-2-(1-indanyl)-1-oxopropyl)alanine benzyl esterYield 72%

Procedure

Using the procedure described in Example 60, but starting with 3-acetylthio-2-(1-indanyl)propanoic acid and alanine benzyl ester, N-[3-acetylthio-2-(1-indanyl)-1-oxopropyl)alanine benzyl ester is obtained in a 72% yield in the form of a white solid, having the following characteristics: m.p.: 95° C.; Rf =0.17 [cyclohexane/ethyl acetate (4:1 by volume)].

Sources & evidence

ORD record
ord-6a1a55c7d69f4be584ff0be181694e27
Source dataset
uspto-grants-1997_01
Patent number
US05591891

Reaction notes

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