Methanol → HCID 66860779, compound

HRID 1696842Notes

Reaction equation

HRID 1696842 reaction equation
C(OC(=O)[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][NH:25][CH2:26][C@@H:27]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][C:37]3C=CC=CC=3)=[C:31]([NH:43][S:44]([CH2:47]CC3C=CC=CC=3)(=[O:46])=[O:45])[CH:30]=2)[OH:28])=[CH:17][CH:16]=1)C1C=CC=CC=1.C[OH:57]>C(O)(=O)C.[OH-].[OH-].[Pd+2].ClCCl>[C:36]([OH:57])(=[O:35])[CH3:37].[C:36]([OH:57])(=[O:35])[CH3:37].[NH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][NH:25][CH2:26][C@@H:27]([C:29]2[CH:34]=[CH:33][C:32]([OH:35])=[C:31]([NH:43][S:44]([CH3:47])(=[O:46])=[O:45])[CH:30]=2)[OH:28])=[CH:17][CH:16]=1

Participants

6

Reactant 2

HCID 887MethanolHCID 66860238HCID 66860238, compound

Product 1

HCID 66860779HCID 66860779, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 9942167Palladium hydroxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of {4-[4-(4-{2-[3-(benzylmethanesulfonylamino)-4-benzyloxyphenyl]-2-(R)-hydroxyethylamino}butyl)phenyl]butyl}carbamic acid benzyl ester (36) (0.41 g, 0.54 mmol), palladium dihydroxide (0.12 g, 10% Pd(OH)2 on carbon, 50% wet), ten drops of acetic acid, methanol (9 mL), and dichloromethane (6 mL) was stirred at rt for 16 h under atmospheric hydrogen pressure. The catalyst was removed by filtration through a Celite pad and the filtrate was concentrated by rotary evaporation and further dried under high vacuum to give the desired amine diacetic acid salt 39 as a white solid (0.30 g, 96%): m/z (ESI) 450 [C23H35N3O4S+H]+.

Workup

  1. customThe catalyst was removed by filtration through a Celite pad
  2. concentrationthe filtrate was concentrated by rotary evaporation
  3. customfurther dried under high vacuum

Sources & evidence

ORD record
ord-5dfdb8751380489ebc0ad06eff1bf5d7
Source dataset
uspto-grants-2012_04
Patent number
US08163758B2

Reaction notes

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