Acetic Acid → HCID 54011543, compound

HRID 2297315Notes

Reaction equation

HRID 2297315 reaction equation
[C:1]([O:5][C:6](=[O:47])[CH2:7][C@H:8]([N:31](CC1C=CC=CC=1)[C@@H](C1C=CC=CC=1)C)[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].CC(O)=O>CCOC(C)=O.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6](=[O:47])[CH2:7][C@H:8]([NH2:31])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 54099226HCID 54099226, compound

Product 1

HCID 54011543HCID 54011543, compoundYield 160.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of (R)-3-[benzyl-((R)-1-phenylethyl)amino]-5-(4′-heptyloxy-biphenyl-4-yl)pentanoic acid tert-butyl ester (2.82 g, 4.45 mmol) in EtOAc (50 ml) were added AcOH (2.5 ml) and Pd(OH)2 on carbon (Pd(OH)2 ca. 20 wt %, 1.07 g), and then the mixture was set under H2 atmosphere. After being stirred for 15 h, the mixture was filtered through a pad of Celite and washed with MeOH. The filtrate and washings were combined, and concentrated in vacuo to give (R)-3-amino-5-(4′-heptyloxybiphenyl-4-yl)pentanoic acid tert-butyl ester (crude, 3.14 g) which was used for the next step without further purification.

Workup

  1. filtrationthe mixture was filtered through a pad of Celite
  2. washwashed with MeOH
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e9e925ff8b6146ad945c71025e4910cb
Source dataset
uspto-grants-2002_12
Patent number
US06489440B1

Reaction notes

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