Water → tert-Butyl N-[4-(2-furyl)-5-(1-oxotetrahydrothiopyran-4-ylcarbonyl)thiazol-2-yl]carbamate

HRID 1967848Notes

Reaction equation

HRID 1967848 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:7]=[C:8]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[S:9][C:10]=1[C:11]([CH:13]1[CH2:18][CH2:17][S:16][CH2:15][CH2:14]1)=[O:12].ClC1C=CC=C(C(OO)=[O:35])C=1.O>C(Cl)(Cl)Cl>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:7]=[C:8]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:25])[CH3:24])[S:9][C:10]=1[C:11]([CH:13]1[CH2:14][CH2:15][S:16](=[O:35])[CH2:17][CH2:18]1)=[O:12]

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 23144236tert-Butyl N-[4-(2-furyl)-5-(tetrahydrothiopyran-4-ylcarbonyl)thiazol-2-yl]carbamate

Product 1

HCID 23144109tert-Butyl N-[4-(2-furyl)-5-(1-oxotetrahydrothiopyran-4-ylcarbonyl)thiazol-2-yl]carbamateYield 69%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Compound 587 (500 mg, 1.27 mmol) was dissolved in chloroform (13 mL), and m-chloroperbenzoic acid (219 mg, 1.27 mmol) was added thereto, followed by stirring at room temperature for 3 hours. The reaction mixture was poured into water, followed by extraction with chloroform. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (ethyl acetate) to afford the entitled Compound 591 (359 mg, 69%).

Workup

  1. extractionfollowed by extraction with chloroform
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe resulting residue was purified through silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-ade34472ad9847468f87813d703e0a43
Source dataset
uspto-grants-2013_04
Patent number
US08420827B2

Reaction notes

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