Methanol → HCID 86649685, compound

HRID 1696828Notes

Reaction equation

HRID 1696828 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]([CH2:46][C@@H:47]([C:49]2[CH:54]=[CH:53][C:52]([O:55][CH2:56][C:57]3C=CC=CC=3)=[C:51]([NH:63][CH:64]=[O:65])[CH:50]=2)[OH:48])[CH2:26][C@H:27]([OH:45])[C:28]2[CH:33]=[CH:32][C:31]([O:34]CC3C=CC=CC=3)=[C:30]([NH:42][CH:43]=[O:44])[CH:29]=2)=[CH:17][CH:16]=1)C1C=CC=CC=1.C[OH:68]>C(O)(=O)C.[OH-].[OH-].[Pd+2].ClCCl>[C:56]([OH:68])(=[O:55])[CH3:57].[C:56]([OH:68])(=[O:55])[CH3:57].[OH:34][C:31]1[CH:32]=[CH:33][C:28]([C@@H:27]([OH:45])[CH2:26][N:25]([CH2:46][C@H:47]([OH:48])[C:49]2[CH:54]=[CH:53][C:52]([OH:55])=[C:51]([NH:63][CH:64]=[O:65])[CH:50]=2)[CH2:24][CH2:23][CH2:22][CH2:21][C:18]2[CH:17]=[CH:16][C:15]([CH2:14][CH2:13][CH2:12][CH2:11][NH2:10])=[CH:20][CH:19]=2)=[CH:29][C:30]=1[NH:42][CH:43]=[O:44]

Participants

6

Reactant 2

HCID 887MethanolHCID 58100160HCID 58100160, compound

Product 1

HCID 86649685HCID 86649685, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 9942167Palladium hydroxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of {4-[4-(4-{bis-[2-(4-benzyloxy-3-formylaminophenyl)-2-(R)-hydroxyethyl]-amino}butyl)phenyl]butyl}carbamic acid benzyl ester (10) (0.17 g, 0.19 mmol), palladium dihydroxide (50 mg, 10% Pd(OH)2 on carbon, 50% wet), eight drops of acetic acid, methanol (10 mL), and dichloromethane (5 mL) was stirred at rt for 18 h under atmospheric hydrogen pressure. The catalyst was filtered 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 13 as a white solid (0.10 mg, 98%); m/z (ESI) 579 [C32H42N4O6+H]+.

Workup

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

Sources & evidence

ORD record
ord-9839e337abf448bca6d8750e7daf8ebd
Source dataset
uspto-grants-2012_04
Patent number
US08163758B2

Reaction notes

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