3-(2-Aminoethyl)-5-(4-ethoxybenzyl)thiazolidine-2,4-dione → (Z)-4-((5-(4-ethoxybenzylidene)-2,4-dioxothiazolidin-3-yl)methyl)benzoic acid

HRID 517611Notes

Reaction equation

HRID 517611 reaction equation
[CH2:1]([O:3][C:4]1[CH:31]=[CH:30][C:7](/[CH:8]=[C:9]2/[C:10](=[O:29])[N:11]([CH2:15][C:16]3[CH:28]=[CH:27][C:19]([C:20]([O:22]C(C)(C)C)=[O:21])=[CH:18][CH:17]=3)[C:12](=[O:14])[S:13]/2)=[CH:6][CH:5]=1)[CH3:2].NCCN1C(=O)C(CC2C=CC(OCC)=CC=2)SC1=O>>[CH2:1]([O:3][C:4]1[CH:31]=[CH:30][C:7](/[CH:8]=[C:9]2/[C:10](=[O:29])[N:11]([CH2:15][C:16]3[CH:17]=[CH:18][C:19]([C:20]([OH:22])=[O:21])=[CH:27][CH:28]=3)[C:12](=[O:14])[S:13]/2)=[CH:6][CH:5]=1)[CH3:2]

Participants

3

Reactant 2

HCID 716970713-(2-Aminoethyl)-5-(4-ethoxybenzyl)thiazolidine-2,4-dioneHCID 71697763(Z)-tert-butyl 4-((5-(4-ethoxybenzylidene)-2,4-dioxothiazolidin-3-yl)methyl)benzoate

Product 1

HCID 56933432(Z)-4-((5-(4-ethoxybenzylidene)-2,4-dioxothiazolidin-3-yl)methyl)benzoic acidYield 97.3%

Procedure

The title compound 28q was prepared by deprotection of tert-butyl group of compound 28p (100 mg, 0.23 mmol). Deprotection following the procedure of compound 6 gave the title compound 28q as a white solid (85 mg, 97.3%).

Sources & evidence

ORD record
ord-9cd36ad9d37345999963616125f3c9f6
Source dataset
uspto-grants-2015_08
Patent number
US09115122B2

Reaction notes

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