Water → HCID 66918907, compound

HRID 1367564Notes

Reaction equation

HRID 1367564 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C@H:9]2[CH2:13][C@H:12]([C:14]#[N:15])[C@@H:11]([O:16][CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[CH2:10]2)=[C:4]([C:23]([F:26])([F:25])[F:24])[CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:35])C=1.[OH2:38]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C@H:9]2[CH2:13][C@H:12]([C:14]#[N:15])[C@@H:11]([O:16][CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[CH2:10]2)(=[O:35])=[O:38])=[C:4]([C:23]([F:25])([F:24])[F:26])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 66918896HCID 66918896, compound

Product 1

HCID 66918907HCID 66918907, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (1S,2R,4R) and (1R,2S,4S)-4-(4-bromo-2-trifluoromethyl-phenylsulfanyl)-2-(tetrahydro-pyran-4-yloxy)-cyclopentanecarbonitrile (345 mg, 0.766 mmol) and mCPBA (472 mg, 70%, 1.915 mmol) in DCM (10 ml) was stirred at room temperature overnight. The mixture was diluted with water and extracted 2 times with DCM. The combined extracts were washed with 15% Na2SO3 solution, saturated NaHCO3 solution, dried (Na2SO4) and evaporated. The remaining colorless solid (370 mg) was used in the next reaction step without further purification. MS (EI): 482.0 (M+H)+.

Workup

  1. extractionextracted 2 times with DCM
  2. washThe combined extracts were washed with 15% Na2SO3 solution, saturated NaHCO3 solution
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe remaining colorless solid (370 mg) was used in the next reaction step without further purification

Sources & evidence

ORD record
ord-39b108777bf0416894566f8429fba8b1
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

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