Isopropanol → HCID 86596961, compound

HRID 2225284Notes

Reaction equation

HRID 2225284 reaction equation
C(S[CH2:5][C@H:6]1[C@@H:15]([NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:14][CH2:13][C:8]2([O:12][CH2:11][CH2:10][O:9]2)[CH2:7]1)(C)C.O[O:28][S:29]([O-:31])=O.[K+].[CH3:33][CH:34](O)[CH3:35]>O>[CH:34]([S:29]([CH2:5][C@H:6]1[C@@H:15]([NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:14][CH2:13][C:8]2([O:12][CH2:11][CH2:10][O:9]2)[CH2:7]1)(=[O:31])=[O:28])([CH3:35])[CH3:33]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 23707502Potassium hydroxy sulfiteHCID 86596962HCID 86596962, compound

Product 1

HCID 86596961HCID 86596961, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of benzyl ((7R,8S)-7-(isopropylthiomethyl)-1,4-dioxa-spiro[4.5]dec-8-yl)-carbamate (2.72 g, 7.16 mmol) in i-PrOH (60 ml) was treated with a solution of Oxone® (8.8 g, 14 mmol) in water (30 ml) and stirred at room temperature for 1 hour. The mixture is diluted with water and extracted into CH2Cl2. The extracts were washed with water, brine and the solvent removed under vacuum. The residue is chromatographed on silica gel (10-50% Ethyl acetate/hexane) to give 2.3 g of benzyl ((7R,8S)-7-(isopropylsulfonylmethyl)-1,4-dioxa-spiro[4.5]dec-8-yl)-carbamate.

Workup

  1. extractionextracted into CH2Cl2
  2. washThe extracts were washed with water, brine
  3. customthe solvent removed under vacuum
  4. customThe residue is chromatographed on silica gel (10-50% Ethyl acetate/hexane)

Sources & evidence

ORD record
ord-14fd71bae8814b82a128fb3969b0607c
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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