HCID 68867115, compound → HCID 68866856, compound

HRID 1988251Notes

Reaction equation

HRID 1988251 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([NH:23]C(OCC2C=CC=CC=2)=O)[CH2:17][NH:18][S:19]([CH3:22])(=[O:21])=[O:20])=[CH:11][C:10]=1[C:34]([CH3:37])([CH3:36])[CH3:35])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>CO.C(Cl)Cl.[OH-].[OH-].[Pd+2]>[NH2:23][CH:16]([CH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:10]([C:34]([CH3:37])([CH3:36])[CH3:35])[CH:11]=1)[CH2:17][NH:18][S:19]([CH3:22])(=[O:21])=[O:20]

Participants

6

Reactant 2

HCID 68867115HCID 68867115, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68866856HCID 68866856, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

N-[3-(4-benzyloxy-3-tert-butylphenyl)-2-benzyloxycarbonylaminopropyl]methanesulfonamide (1.2 g, 2.29 mmol) was dissolved in a mixture of methanol (23 ml) and methylene chloride (5 ml), mixed with palladium hydroxide/carbon (0.60 g) and stirred for 12 hours in a hydrogen atmosphere. After filtering off insoluble material using Celite, the filtrate was concentrated to give crude N-[2-amino-3-(4-benzyloxy-3-tert-butylphenyl)propyl]methanesulfonamide (0.68 g).

Workup

  1. filtrationAfter filtering off insoluble material
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-aeb562485894470f9ea7e46a6f6e36e2
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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