D-Cysteine → N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid 2-ethyl ester

HRID 1503166

Reaction equation

HRID 1503166 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C:6]1([CH3:14])[NH:10][CH:9]([C:11]([OH:13])=[O:12])[CH2:8][S:7]1)=[O:5].N[C@@H:16]([C:19](O)=[O:20])CS>>[CH3:1][CH2:2][O:3][C:4]([C:6]1([CH3:14])[N:10]([C:19](=[O:20])[CH3:16])[CH:9]([C:11]([OH:13])=[O:12])[CH2:8][S:7]1)=[O:5]

Participants

3

Reactant 2

HCID 92851D-CysteineHCID 866809292-Methylthiazolidine-2,4-dicarboxylic acid 2-ethyl ester

Product 1

HCID 54760676N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid 2-ethyl ester

Procedure

By a method similar to that in Synthetic Example 7 except for the use of 2-methylthiazolidine-2,4-dicarboxylic acid 2-ethyl ester synthesized from D-cysteine by a method similar to that in Reference Example 2, N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid 2-ethyl ester was obtained (with the ratio of cis form:trans form of about 43:57 as confirmed by NMR).

Sources & evidence

ORD record
ord-d299629c64024410895b804341dc4ff2
Source dataset
uspto-grants-2015_12
Patent number
US09212154B2

Linked notes

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