Potassium Carbonate → (Z)-tert-butyl 2-(5-(4-ethoxybenzylidene)-2,4-dioxothiazolidin-3-yl)acetate

HRID 517601Notes

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][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].C(=O)([O-])[O-].[K+].[K+].C(OC1C=CC(/C=C2/C(=O)N(CCC)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]([CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:12](=[O:14])[S:13]/2)=[CH:6][CH:5]=1)[CH3:2]

Participants

Reactant 4

HCID 11430Potassium Carbonate

HCID 79177tert-Butyl bromoacetate

HCID 5878179(Z)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione

HCID 71697554(Z)-5-(4-ethoxybenzylidene)-3-propylthiazolidine-2,4-dione

Product 1

HCID 5958148(Z)-tert-butyl 2-(5-(4-ethoxybenzylidene)-2,4-dioxothiazolidin-3-yl)acetate

Procedure

The title compound 28g was prepared from compound 2 (249 mg, 1.00 mmol), tert-butyl bromoacetate (215 mg, 1.10 mmol) and potassium carbonate (276 mg, 2.00 mmol) in a manner similar to that described for 28d in 99.0% (360 mg) yield as a pale-yellow solid.

Workup

customyield as a pale-yellow solid

Sources & evidence

ORD record: ord-41e7b1c1888c4d4a8e1786506b0976ea
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115122B2

Reaction notes

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