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

HRID 1503173Notes

Reaction equation

[CH3:1][C:2]1([C:10]([OH:12])=[O:11])[NH:6][CH:5]([C:7]([OH:9])=[O:8])[CH2:4][S:3]1.N[CH:14]([C:17](O)=[O:18])CS>>[C:17]([N:6]1[CH:5]([C:7]([OH:9])=[O:8])[CH2:4][S:3][C:2]1([CH3:1])[C:10]([OH:12])=[O:11])(=[O:18])[CH3:14]

Participants

Reactant 2

HCID 594DL-cysteine

HCID 983422-Methyl-2,4-thiazolidinedicarboxylic acid

Product 1

HCID 451223662,4-Thiazolidinedicarboxylic acid, 3-acetyl-2-methyl-Yield 44%

Procedure

By an operation similar to that in Synthetic Example 16 and using 2-methylthiazolidine-2,4-dicarboxylic acid synthesized from DL-cysteine by a method similar to that in Reference Example 1, N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid (cis form) was obtained as an amorphous substance (yield 44%).

Sources & evidence

ORD record: ord-ba6b81cb18364bcea2395ac2e9d0a307
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212154B2

Reaction notes

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