m-Chloroperbenzoic acid → HCID 68353077, compound

HRID 1844668Notes

Reaction equation

HRID 1844668 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[CH2:12]([O:14][C:15](=[O:38])[O:16][C:17]1[CH:18]([CH2:31][CH:32]2[CH2:37][CH2:36][S:35][CH2:34][CH2:33]2)[NH:19][C:20](=[O:30])[C:21]=1[C:22]1[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][C:23]=1[CH3:29])[CH3:13]>C(Cl)Cl>[CH2:12]([O:14][C:15](=[O:38])[O:16][C:17]1[CH:18]([CH2:31][CH:32]2[CH2:37][CH2:36][S:35](=[O:9])[CH2:34][CH2:33]2)[NH:19][C:20](=[O:30])[C:21]=1[C:22]1[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][C:23]=1[CH3:29])[CH3:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 68299279HCID 68299279, compound

Product 1

HCID 68353077HCID 68353077, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of m-CPBA (189 mg, 1.1 mmol) in 5 ml of CH2Cl2 was added slowly to a stirred solution of carbonic acid 4-(2,5-dimethyl-phenyl)-5-oxo-2-(tetrahydro-thiopyran-4-ylmethyl)-2,5-dihydro-1H-pyrrol-3-yl ester ethyl ester (compound P1.2) (390 mg, 1.0 mmol) in 10 ml CH2Cl2 and the reaction mixture was stirred at room temperature for 1 h. Then, the resulting mixture was washed with saturated NaHCO3 (aq) and aqueous Na2S2O3, respectively. The organic layer was dried over sodium sulfate, filtered and concentrated under reduce pressure. The residue was purified by chromatography on silica gel. Yield: 100 mg of carbonic acid 4-(2,5-dimethyl-phenyl)-5-oxo-2-(1-oxo-hexahydro-1λ4-thiopyran-4-ylmethyl)-2,5-dihydro-1H-pyrrol-3-yl ester ethyl ester (compound P1.4) as a solid, mp 103-106° C.

Workup

  1. washThen, the resulting mixture was washed with saturated NaHCO3 (aq) and aqueous Na2S2O3
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-f41c00c8612f40c59ef4914ece5b0102
Source dataset
uspto-grants-2015_02
Patent number
US08946453B2

Reaction notes

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