Sodium Hydroxide → (4S)-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid

HRID 1744197Notes

Reaction equation

[CH3:1][C:2]1([CH3:10])[S:6][CH2:5][NH:4][C@H:3]1[C:7](N)=[O:8].[OH-].[Na+].CC1(C)SCNC1C(N)=[O:20]>C(O)C(C)C>[CH3:1][C:2]1([CH3:10])[S:6][CH2:5][NH:4][C@H:3]1[C:7]([OH:20])=[O:8]

Participants

Conditions

Temperature: 110 °C

Procedure

Optically active (4S)-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid amide (5.0 g, 31.3 mmol), sodium hydroxide (0.25 g, 11.2 mmol) and i-butyl alcohol (50 ml) were placed in a 200-ml three-necked flask attached with a stirrer, thermometer and reflux condenser and stirred at 110° C. for 2 hours. After completion of the reaction, the reaction mixture was analyzed by liquid chromatography. As a result, it was found that the residual ratio of the 5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid amide was 82.3%, and the racemization ratio of the optically active (4S)-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid amide was 97.5%.

Workup

customattached with a stirrer
temperaturethermometer and reflux condenser
customAfter completion of the reaction

Sources & evidence

ORD record: ord-ff889c122c8349cd88d1eb63ed3c94f9
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07015029B2

Reaction notes

Loading…