Penicillamine methyl ester → benzyl (RS)-alpha-[[[(S)-2-amino-2-(methoxycarbonyl)1,1-dimethylethyl]thio]methyl]hydrocinnamate
Reaction equation
[CH3:1][O:2][C:3](=[O:10])[C@H:4]([C:6]([SH:9])([CH3:8])[CH3:7])[NH2:5].[CH2:11]([C:18](=[CH2:29])[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[NH2:5][C@@H:4]([C:3]([O:2][CH3:1])=[O:10])[C:6]([S:9][CH2:29][CH:18]([CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:19]([O:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:20])([CH3:8])[CH3:7]Participants
Procedure
In an analogous manner to that described in Example 1, paragraph (d), by adding L-penicillamine methyl ester (J. Chem. Soc. Dalton Trans. 1984, 1333) to benzyl 2-benzylacrylate there was obtained benzyl (RS)-α-[[[(S)-2-amino-2-(methoxycarbonyl)1,1-dimethylethyl]thio]methyl]hydrocinnamate, MS: 416 (M+H)+, as an oil, the amino group of which was protected according to a general procedure known from the literature by reaction with di-tert-butyl dicarbonate. Subsequent oxidation with 3-chloroperbenzoic acid in methylene chloride gave benzyl (RS)-α-[[[(S)-2-(1-tert-butoxyformamido)-2-(methoxycarbonyl)-1,1-dimethylethyl]sulfonyl]methyl]hydrocinnamate as a colourless oil, MS: 448 (M-Boc+H)+. p1 (1) Catalytic hydrogenation of benzyl (RS)-α-[[[(S)-2-(1-tert-butoxy- formamido)-2-(methoxycarbonyl)-1,1-dimethylethyl]sulfonyl]-methyl]hydrocinnamate analogously to Example 1, paragraph (g), yielded (RS)-α-[[[(S)-2-(1-tert-butoxyformamido)-2-(methoxycarbonyl)-l,1dimethylethyl]sulfonyl]methyl]hydrocinnamic acid as a colourless solid, MS: 401 (M-C4H8)+.
Sources & evidence
- ORD record
- ord-a33a466fcd714862bb8ce6d09408bcfd
- Source dataset
- uspto-grants-1995_02
- Patent number
- US05393875
Reaction notes
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