Methanol → HCID 66859659, compound

HRID 1696844Notes

Reaction equation

HRID 1696844 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][N:25]([CH2:55][C@@H:56]([C:58]2[CH:63]=[CH:62][C:61]([O:64][CH2:65][C:66]3C=CC=CC=3)=[C:60]([NH:72][S:73]([CH2:76]CC3C=CC=CC=3)(=[O:75])=[O:74])[CH:59]=2)[OH:57])[CH2:26][C@H:27]([OH:54])[C:28]2[CH:33]=[CH:32][C:31]([O:34]CC3C=CC=CC=3)=[C:30]([NH:42][S:43]([CH2:46]CC3C=CC=CC=3)(=[O:45])=[O:44])[CH:29]=2)=[CH:17][CH:16]=1)C1C=CC=CC=1.C[OH:86]>C(O)(=O)C.[OH-].[OH-].[Pd+2].ClCCl>[C:65]([OH:86])(=[O:64])[CH3:66].[C:65]([OH:86])(=[O:64])[CH3:66].[NH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][N:25]([CH2:55][C@H:56]([OH:57])[C:58]2[CH:63]=[CH:62][C:61]([OH:64])=[C:60]([NH:72][S:73]([CH3:76])(=[O:74])=[O:75])[CH:59]=2)[CH2:26][C@@H:27]([C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([NH:42][S:43]([CH3:46])(=[O:45])=[O:44])[CH:29]=2)[OH:54])=[CH:19][CH:20]=1

Participants

6

Reactant 2

HCID 887MethanolHCID 86649689HCID 86649689, compound

Product 1

HCID 66859659HCID 66859659, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 9942167Palladium hydroxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of (4-{4-[4-(bis-{2-[3-(benzylmethanesulfonylamino)-4-benzyloxyphenyl]-2-(R)-hydroxyethyl}amino)butyl]phenyl}butyl)carbamic acid benzyl ester (38) (0.45 g, 0.383 mmol), palladium dihydroxide (0.12 g, 10% Pd(OH)2 on carbon, 50% wet), ten drops of acetic acid, methanol (12 mL), and dichloromethane (6 mL) was stirred at rt for 18 h under atmospheric hydrogen pressure. The catalyst was removed by vacuum 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 41 as a white solid (0.30 g, 98%): m/z (ESI) 679 [C32H42N4O6+H]+.

Workup

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

Sources & evidence

ORD record
ord-cfd3b565fe05452d95c6d29c1156c4cc
Source dataset
uspto-grants-2012_04
Patent number
US08163758B2

Reaction notes

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