Methanol → HCID 86649682, compound

HRID 1696826Notes

Reaction equation

HRID 1696826 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][CH:44]=[O:45])[CH:30]=2)[OH:28])=[CH:17][CH:16]=1)C1C=CC=CC=1.C[OH:48]>C(O)(=O)C.[OH-].[OH-].[Pd+2].ClCCl>[C:36]([OH:48])(=[O:35])[CH3:37].[C:36]([OH:48])(=[O:35])[CH3:37].[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][NH:25][CH2:26][C@@H:27]([C:29]2[CH:34]=[CH:33][C:32]([OH:35])=[C:31]([NH:43][CH:44]=[O:45])[CH:30]=2)[OH:28])=[CH:19][CH:20]=1

Participants

6

Reactant 2

HCID 887MethanolHCID 86649684HCID 86649684, compound

Product 1

HCID 86649682HCID 86649682, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 9942167Palladium hydroxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of [4-(4-{4-[2-(4-benzyloxy-3-formylaminophenyl)-2-(R)-hydroxyethylamino]butyl}phenyl)butyl]carbamic acid benzyl ester (8) (84 mg, 0.14 mmol), palladium dihydroxide (28 mg, 10% Pd(OH)2 on carbon, 50% wet), three drops of acetic acid, methanol (5 mL), and dichloromethane (5 mL) was stirred at rt for 16 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 11 as a yellow solid (69 mg, 99%): 1H NMR (500 MHz, CD3OD) δ 1.68 (m, 8H), 1.93 (s, 6H), 2.63 (m, 4H), 2.91 (m, 2H), 3.08 (m, 4H), 4.83 (m, 1H), 6.88 (d, 1H), 7.05 (d, 1H), 7.11 (s, 4H), 8.10 (s, 1H), 8.30 (s, 1H); m/z (ESI) 400 [C23H33N3O3+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-8262152e6f214260b5fa9c1339592fea
Source dataset
uspto-grants-2012_04
Patent number
US08163758B2

Reaction notes

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