(Z)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione → (Z)-tert-butyl (2-(5-(4-ethoxybenzylidene)-2,4-dioxothiazolidin-3-yl)propyl)carbamate

HRID 517581Notes

Reaction equation

HRID 517581 reaction equation
[CH2:1]([O:3][C:4]1[CH:17]=[CH:16][C:7](/[CH:8]=[C:9]2/[C:10](=[O:15])[NH:11][C:12](=[O:14])[S:13]/2)=[CH:6][CH:5]=1)[CH3:2].Br[CH:19]([CH3:29])[CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25].C(OC1C=CC(/C=C2/C(=O)N(CCCNC(=O)OC(C)(C)C)C(=O)S/2)=CC=1)C>>[CH2:1]([O:3][C:4]1[CH:17]=[CH:16][C:7](/[CH:8]=[C:9]2/[C:10](=[O:15])[N:11]([CH:19]([CH3:29])[CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:12](=[O:14])[S:13]/2)=[CH:6][CH:5]=1)[CH3:2]

Participants

4

Reactant 3

HCID 5878179(Z)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dioneHCID 14458310Tert-butyl (2-bromopropyl)carbamateHCID 71697170(Z)-tert-butyl (3-(5-(4-ethoxybenzylidene)-2,4-dioxothiazolidin-3-yl)propyl)carbamate

Product 1

HCID 86724393(Z)-tert-butyl (2-(5-(4-ethoxybenzylidene)-2,4-dioxothiazolidin-3-yl)propyl)carbamateYield 15.4%

Procedure

The title compound 21c was prepared from compound 2 (300 mg, 1.20 mmol) and tert-butyl (2-bromopropyl)carbamate (286 mg, 1.20 mg) in a manner similar to that described for 21a. Yield=15.4%, 75 mg.

Sources & evidence

ORD record
ord-815543bf6a574b50a877bea317bbf8b1
Source dataset
uspto-grants-2015_08
Patent number
US09115122B2

Reaction notes

Loading…