Acetyl chloride → HCID 86680933, compound

HRID 1503178Notes

Reaction equation

HRID 1503178 reaction equation
Cl.[CH3:2][O:3][C:4]([CH:6]1[NH:10][CH:9]([C:11]([O:13][CH3:14])=[O:12])[CH2:8][S:7]1)=[O:5].[C:15](Cl)(=[O:17])[CH3:16].C(N(CC)CC)C>>[CH3:2][O:3][C:4]([CH:6]1[N:10]([C:15](=[O:17])[CH3:16])[CH:9]([C:11]([O:13][CH3:14])=[O:12])[CH2:8][S:7]1)=[O:5]

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 86680931HCID 86680931, compound

Product 1

HCID 86680933HCID 86680933, compound

Procedure

Thiazolidine-2,4-dicarboxylic acid 2,4-dimethyl ester hydrochloride (0.50 g, 2.07 mmol) was subjected to acylation with acetyl chloride (0.22 ml, 3.09 mmol) in the presence of triethylamine (0.58 ml, 4.17 mmol) to give N-acetylthiazolidine-2,4-dicarboxylic acid 2,4-dimethyl ester (with the ratio of two kinds of stereoisomers of about 49:51 as confirmed by NMR) as a pale-yellow oil (0.42 g, 83.0%).

Sources & evidence

ORD record
ord-08f406401d7046e88447df647566b4b4
Source dataset
uspto-grants-2015_12
Patent number
US09212154B2

Reaction notes

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