(Z)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione → (Z)-di-tert-butyl (2-(5-(4-ethoxybenzylidene)-2,4-dioxothiazolidin-3-yl)propane-1,3-diyl)dicarbamate

HRID 517583Notes

Reaction equation

HRID 517583 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]([CH2:29][NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[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]([CH2:29][NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:25])[CH3:26])[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 71697170(Z)-tert-butyl (3-(5-(4-ethoxybenzylidene)-2,4-dioxothiazolidin-3-yl)propyl)carbamateHCID 86724396Di-tert-butyl (2-bromopropane-1,3-diyl)dicarbamate

Product 1

HCID 86724395(Z)-di-tert-butyl (2-(5-(4-ethoxybenzylidene)-2,4-dioxothiazolidin-3-yl)propane-1,3-diyl)dicarbamateYield 23.9%

Procedure

The title compound 21e was prepared from compound 2 (292 mg, 1.17 mmol) and di-tert-butyl (2-bromopropane-1,3-diyl)dicarbamate (413 mg, 1.17 mg) in a manner similar to that described for 21a. Yield=23.9%, 130 mg.

Sources & evidence

ORD record
ord-0a1070ca5ae749c88731f3f5a5ebb805
Source dataset
uspto-grants-2015_08
Patent number
US09115122B2

Reaction notes

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