Benzaldehyde → 2-(4-Oxo-2-phenyl-3-((pyridin-4-yl)methyl)thiazolidin-5-yl)acetic acid

HRID 1695896Notes

Reaction equation

[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:9]1[CH:14]=[CH:13][C:12]([CH2:15]CN)=[CH:11][CH:10]=1.[SH:18][CH:19]([CH2:23][C:24]([OH:26])=[O:25])[C:20](O)=[O:21].C[N:28](C=O)C>O>[O:21]=[C:20]1[CH:19]([CH2:23][C:24]([OH:26])=[O:25])[S:18][CH:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:28]1[CH2:15][C:12]1[CH:11]=[CH:10][N:9]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of benzaldehyde (0.75 mmol, 79.6 mg) and 2-(pyridin-4-yl)ethanamine (97.3 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. LC/MS (10% to 99%): M/Z (M+H)+ (obs)=329; tR=1.95.

Workup

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

Sources & evidence

ORD record: ord-3003de5c401d42d1b7768280a96baf93
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163737B2

Reaction notes

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