HCID 69035575, compound → HCID 69036612, compound

HRID 351395Notes

Reaction equation

HRID 351395 reaction equation
C(OC(=O)[NH:10][C@H:11]1[CH2:16][CH2:15][C@@H:14]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13][C@H:12]1[CH2:25][S:26]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)(=[O:28])=[O:27])C1C=CC=CC=1.[H][H]>CO.[OH-].[OH-].[Pd+2]>[C:21]([O:20][C:18](=[O:19])[NH:17][C@@H:14]1[CH2:15][CH2:16][C@H:11]([NH2:10])[C@H:12]([CH2:25][S:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)(=[O:28])=[O:27])[CH2:13]1)([CH3:24])([CH3:22])[CH3:23]

Participants

5

Reactant 2

HCID 69035575HCID 69035575, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69036612HCID 69036612, compoundYield 92.9%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of (1S,2R,4R)-(2-benzene-sulfonylmethyl-4-tert-butoxycarbonylaminocyclohexyl)carbamic acid benzyl ester (2.96 g, 5.9 mmol) and 20% palladium hydroxide on charcoal (Pearlman's catalyst, 2.0 g) in methanol (100 mL) was stirred under one atmosphere of hydrogen at room temperature for 16.5 h. The mixture was filtered through Celite, and the solids were washed with methanol. The filtrate was concentrated under vacuum and the residue was dissolved in dichloromethane. The solution was dried over sodium sulfate and concentrated under vacuum to provide (1R,3R,4S)-(4-amino-3-benzenesulfonylmethylcyclohexyl)-carbamic acid tert-butyl ester (2.02 g) as a white glassy solid, used without further purification. MS found: (M+H)+=369.62.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washthe solids were washed with methanol
  3. concentrationThe filtrate was concentrated under vacuum
  4. dissolutionthe residue was dissolved in dichloromethane
  5. dry with materialThe solution was dried over sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f38a791707c14b578768c1cf1fcf2d30
Source dataset
uspto-grants-2007_02
Patent number
US07183270B2

Reaction notes

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