Benzaldehyde → 2-(3-Methyl-4-oxo-2-phenylthiazolidin-5-yl)acetic acid

HRID 1172299Notes

Reaction equation

[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:10][NH2:11].[SH:12][CH:13]([CH2:17][C:18]([OH:20])=[O:19])[C:14](O)=[O:15]>CN(C=O)C.O>[CH3:10][N:11]1[C:14](=[O:15])[CH:13]([CH2:17][C:18]([OH:20])=[O:19])[S:12][CH:1]1[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of benzaldehyde (0.75 mmol, 79.6 mg) and methylamine hydrochloride (60.8 mg, 0.9 mmol) in DMF (0.5 ml) with 4 Å molecular sieves was heated at 80° C. for 2 hours. A solution of mercaptosuccinic acid (1.13 mmol, 168 mg) in DMF (0.2 ml) was added and the reaction was heated at 80° C. for an additional 16 hours. The reaction mixture was diluted with water and extracted with EtOAc. The organic layer was washed with 1N HCl, water and evaporated to dryness to give the desired product which was used without further purification.

Workup

extractionextracted with EtOAc
washThe organic layer was washed with 1N HCl, water
customevaporated to dryness

Sources & evidence

ORD record: ord-c4e9b0117f7f4f3b8d81485e9fc7148c
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834000B2

Reaction notes

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