(Z)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione → (Z)-tert-butyl (1-(5-(4-ethoxybenzylidene)-2,4-dioxothiazolidin-3-yl)propan-2-yl)carbamate

HRID 517580Notes

Reaction equation

HRID 517580 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[CH2:19][CH:20]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH3:21].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]([CH2:21][CH:20]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:26])([CH3:28])[CH3:27])[CH3:19])[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 22274345t-Butyl (1-bromopropan-2-yl)carbamateHCID 71697170(Z)-tert-butyl (3-(5-(4-ethoxybenzylidene)-2,4-dioxothiazolidin-3-yl)propyl)carbamate

Product 1

HCID 86724392(Z)-tert-butyl (1-(5-(4-ethoxybenzylidene)-2,4-dioxothiazolidin-3-yl)propan-2-yl)carbamateYield 22.5%

Procedure

The title compound 21b was prepared from compound 2 (260 mg, 1.04 mmol) and tert-butyl (1-bromopropan-2-yl)carbamate (247 mg, 1.04 mmol) in a manner similar to that described for 21a. Yield=22.5%, 95.0 mg.

Sources & evidence

ORD record
ord-fe4d98ded096494da4effb479bc0665a
Source dataset
uspto-grants-2015_08
Patent number
US09115122B2

Reaction notes

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