tert-Butyl acrylate → HCID 178469100, compound

HRID 1158091Notes

Reaction equation

HRID 1158091 reaction equation
[O:1]=[C:2]1[CH:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[S:5][C:4]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:22])([F:21])[F:20])=[N:3]1.[C:23]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])(=[O:26])[CH:24]=[CH2:25].C1CCN2C(=NCCC2)CC1>CCO>[C:28]([O:27][C:23](=[O:26])[CH2:24][CH2:25][C:6]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[S:5][C:4]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:22])([F:20])[F:21])=[N:3][C:2]1=[O:1])([CH3:31])([CH3:30])[CH3:29]

Participants

5

Reactant 3

HCID 15458tert-Butyl acrylateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178470560HCID 178470560, compound

Product 1

HCID 178469100HCID 178469100, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The above compounds were prepared according to the procedure reported in the literature: see S. Muthusamy Synth. Commun. 2002, 32, 3247. To a stirred solution of ethyl 4-oxo-2-(2-(trifluoromethyl)phenylamino)-4,5-dihydrothiazole-5-carboxylate (1.1 g, 3.3 mol), tert-butyl acrylate (Aldrich, 2.5 mL, 16.5 mmol) in EtOH (10 mL) was added DBU (Aldrich, 0.25 mL, 1.6 mmol). The mixture was stirred at r.t. overnight and concentrated in vacuo. The crude product was purified by silica gel chromatography. MS: 461 (M+1).

Workup

  1. customThe above compounds were prepared
  2. concentrationconcentrated in vacuo
  3. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-5992af53b137472492bdaa9b92e8f6a3
Source dataset
uspto-grants-2010_10
Patent number
US07807700B2

Reaction notes

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