Isopropanol → HCID 86596903, compound

HRID 1171589Notes

Reaction equation

HRID 1171589 reaction equation
[CH:1]([O:4][CH:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12](=[O:21])[O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C@H:7]([CH2:22]SC(C)C)[CH2:6]1)([CH3:3])[CH3:2].O[O:28][S:29]([O-:31])=O.[K+].[CH3:33][CH:34](O)[CH3:35]>O>[CH:1]([O:4][CH:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12](=[O:21])[O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C@H:7]([CH2:22][S:29]([CH:34]([CH3:35])[CH3:33])(=[O:31])=[O:28])[CH2:6]1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 23707502Potassium hydroxy sulfiteHCID 86596904HCID 86596904, compound

Product 1

HCID 86596903HCID 86596903, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A sample of benzyl (1S,2R)-4-isopropoxy-2-(isopropylthiomethyl)cyclohexylcarbamate (27.59 mMol) was dissolved in iPrOH (200 mL) prior to the addition of OXONE™ (33.92 g, 55.18 mMol) as a solution in 300 mL of water. The reaction was stirred at rt overnight. Partitioned between EtOAc and water. Aqueous layer was re-extracted with EtOAc and combined organic layer was washed with brine and dried (MgSO4). Filtered, concentrated and flash chromatographed to yield benzyl (1S,2R)-4-isopropoxy-2-(isopropylsulfonylmethyl)cyclohexylcarbamate as a clear oil (7.73 g, 68% over Steps 5 and 6). MS found: (M+H)+=412.35.

Workup

  1. customPartitioned between EtOAc and water
  2. extractionAqueous layer was re-extracted with EtOAc and combined organic layer
  3. washwas washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationFiltered
  6. concentrationconcentrated
  7. customflash chromatographed

Sources & evidence

ORD record
ord-34f6e6893abb4b0bb151895afa90343a
Source dataset
uspto-grants-2010_11
Patent number
US07829571B2

Reaction notes

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