Sodium Chloride → (RS)-S-ethyl-N-({[(1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl]oxy}carbonyl)-S-(4-nitrophenyl)sulfoximide

HRID 1391476Notes

Reaction equation

HRID 1391476 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([CH2:13][CH3:14])(=[NH:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl[C:16]([O:18][CH:19]1[CH:24]([CH:25]([CH3:27])[CH3:26])[CH2:23][CH2:22][CH:21]([CH3:28])[CH2:20]1)=[O:17].[Na+].[Cl-]>N1C=CC=CC=1>[CH2:13]([S:10]([C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)(=[N:12][C:16]([O:18][C@@H:19]1[CH2:20][C@H:21]([CH3:28])[CH2:22][CH2:23][C@H:24]1[CH:25]([CH3:27])[CH3:26])=[O:17])=[O:11])[CH3:14]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 151928Menthyl chloroformateHCID 59550863Ethyl(imino)(4-nitrophenyl)-_6-sulfanone

Product 1

HCID 59674037(RS)-S-ethyl-N-({[(1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl]oxy}carbonyl)-S-(4-nitrophenyl)sulfoximide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

100 mg (0.47 mmol) of (RS)-S-(4-nitrophenyl)-S-ethyl sulfoximide in 4.40 ml of pyridine is mixed drop by drop at room temperature with 0.46 ml (2.17 mmol) of (+) menthyl chloroformate. The batch is stirred for 4 hours at room temperature and then added to dilute NaCl solution. It is extracted from ethyl acetate. The combined organic phases are dried (Na2SO4), filtered and concentrated by evaporation. The remaining residue is purified by chromatography (hexane/ethyl acetate 1:1). 161 mg (0.41 mmol, corresponding to 87% of theory) of the product is obtained.

Workup

  1. extractionIt is extracted from ethyl acetate
  2. dry with materialThe combined organic phases are dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated by evaporation
  5. customThe remaining residue is purified by chromatography (hexane/ethyl acetate 1:1)
  6. custom161 mg (0.41 mmol, corresponding to 87% of theory) of the product is obtained

Sources & evidence

ORD record
ord-0c97b1d9230b4259a22b3bffbc9282a9
Source dataset
uspto-grants-2008_03
Patent number
US07338958B2

Reaction notes

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