Dichloromethane → HCID 23154177, compound

HRID 639427Notes

Reaction equation

HRID 639427 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.C(Cl)Cl.[C:15]([S:19]([NH:21][CH:22]1[CH2:27][CH2:26][CH:25]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:24][CH2:23]1)=[O:20])([CH3:18])([CH3:17])[CH3:16]>C(OCC)(=O)C>[C:15]([S:19]([NH:21][CH:22]1[CH2:27][CH2:26][CH:25]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:24][CH2:23]1)(=[O:9])=[O:20])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 23154158HCID 23154158, compound

Product 1

HCID 23154177HCID 23154177, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Metachloroperbenzoic acid (1.25 g) was added, under cooling with ice, to a methylene chloride solution (10 mL) containing ethyl 4-tert-butylsulfinylaminocyclohexane-carboxylate (1.0 g) as prepared by the above-described preparation method, and stirring was effected at room temperature for 3 hrs. The reaction mixture, after being diluted with ethyl acetate, was washed with an aqueous saturated sodium-hydrogencarbonate and sodium-chloride solutions successively, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resultant residue was separated and purified by silica-gel chromatography (C-300, hexane:ethyl acetate=1:1) to give ethyl 4-tert-butylsulfonylamino-cyclohexanecarboxylate composed mainly of the trans isomer (673 mg).

Workup

  1. customas prepared by the above-described preparation method
  2. washwas washed with an aqueous saturated sodium-hydrogencarbonate and sodium-chloride solutions successively
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resultant residue was separated
  6. custompurified by silica-gel chromatography (C-300, hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-4921ed761e17410fbefda6995c40cf15
Source dataset
uspto-grants-2010_04
Patent number
US07691860B2

Reaction notes

Loading…