DL-cysteine → 2,4-Thiazolidinedicarboxylic acid, 3-acetyl-2-methyl-

Reaction equation

CC[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[CH:16]([C:19](O)=[O:20])CS>>[C:19]([N:10]1[CH:9]([C:11]([OH:13])=[O:12])[CH2:8][S:7][C:6]1([CH3:14])[C:4]([OH:3])=[O:5])(=[O:20])[CH3:16]

Participants

Reactant 2

HCID 594DL-cysteine

HCID 866809292-Methylthiazolidine-2,4-dicarboxylic acid 2-ethyl ester

Product 1

HCID 451223662,4-Thiazolidinedicarboxylic acid, 3-acetyl-2-methyl-

Procedure

By an operation similar to that in Synthetic Example 13 and using 2-methylthiazolidine-2,4-dicarboxylic acid 2-ethyl ester synthesized from DL-cysteine by a method similar to that in Reference Example 2, N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid (trans form) was obtained as a white solid (yield 70%).

Sources & evidence

ORD record: ord-f49e56588c904010995cbe734114a4ee
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212154B2

Reaction notes

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