m-Chloroperbenzoic acid → HCID 10361232, compound

HRID 855547Notes

Reaction equation

HRID 855547 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[CH:12]1(/[CH:17]=[C:18](\[C:27]2[CH:28]=[N:29][C:30]([S:33][CH3:34])=[CH:31][CH:32]=2)/[C:19]([NH:21][C:22]2[S:23][CH:24]=[CH:25][N:26]=2)=[O:20])[CH2:16][CH2:15][CH2:14][CH2:13]1>C(Cl)Cl.CCOC(C)=O>[CH:12]1(/[CH:17]=[C:18](\[C:27]2[CH:28]=[N:29][C:30]([S:33]([CH3:34])=[O:9])=[CH:31][CH:32]=2)/[C:19]([NH:21][C:22]2[S:23][CH:24]=[CH:25][N:26]=2)=[O:20])[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 10088931HCID 10088931, compound

Product 1

HCID 10361232HCID 10361232, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of mCPBA (85% pure, 64 mg, 318 μmol) in CH2Cl2 (1 mL) was added over 5 min to a stirred solution of (E)-3-cyclopentyl-2-(6-methylsulfanylpyridin-3-yl)-N-thiazol-2-ylacrylamide (EXAMPLE 5, 110 mg, 318 μmol) in CH2Cl2 (5 mL) at 0° C. After 4.5 h at 0° C., the reaction mixture was diluted with EtOAc (40 mL). The resulting solution was washed with H2O-saturated aqueous NaHCO3 (1:1, 2×20 mL) and brine (20 mL), before being dried (MgSO4). Filtration, solvent evaporation, and column chromatography (EtOAc then THF) provided the title compound: RTA=3.32 min; m/z (ES+)=362.1 [M+H]+.

Workup

  1. washThe resulting solution was washed with H2O-saturated aqueous NaHCO3 (1:1, 2×20 mL) and brine (20 mL)
  2. dry with materialbefore being dried (MgSO4)
  3. filtrationFiltration, solvent evaporation, and column chromatography (EtOAc

Sources & evidence

ORD record
ord-a2cf5511864c418ebfdc6b5eb39398c0
Source dataset
uspto-grants-2007_08
Patent number
US07262196B2

Reaction notes

Loading…