L-(+)-Cysteine → HCID 89483261, compound

HRID 1503174Notes

Reaction equation

[NH2:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][SH:4].[CH3:8][O:9][C:10](=[O:14])[C:11]([CH3:13])=O.[C:15](Cl)(=[O:17])[CH3:16].C(=O)([O-])[O-].[K+].[K+]>>[CH3:8][O:9][C:10]([C:11]1([CH3:13])[N:1]([C:15](=[O:17])[CH3:16])[CH:2]([C:5]([OH:7])=[O:6])[CH2:3][S:4]1)=[O:14]

Participants

Reactant 4

HCID 5862L-(+)-Cysteine

HCID 6367Acetyl chloride

HCID 11430Potassium Carbonate

HCID 11748Methyl pyruvate

Product 1

HCID 89483261HCID 89483261, compound

Procedure

In the same manner as in Reference Example 2, L-2-methylthiazolidine-2,4-dicarboxylic acid 2-methyl ester was synthesized from L-cysteine and pyruvic acid methyl ester, and the compound was subjected to acetylation with acetyl chloride in the presence of potassium carbonate to give N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid 2-methyl ester (with the ratio of cis form:trans form of about 44:56 as confirmed by NMR) as a white solid (80.2%). 1H-NMR (DMSO-d6,400 MHz): δ;

Sources & evidence

ORD record: ord-ab2367fee713490887c5c58ac2c93f38
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212154B2

Reaction notes

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