HCID 178418361, compound → HCID 178447302, compound

HRID 1609196Notes

Reaction equation

HRID 1609196 reaction equation
C([O:8][C:9](=[O:39])[C@H:10]([CH:36]([CH3:38])[CH3:37])[N:11]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]2[NH:35][N:34]=[N:33][N:32]=2)=[CH:21][CH:20]=1)[C:12](=[O:17])[CH2:13][CH2:14][CH2:15][CH3:16])C1C=CC=CC=1.[H][H]>CO.[Pd]>[C:9]([C@@H:10]([N:11]([C:12](=[O:17])[CH2:13][CH2:14][CH2:15][CH3:16])[CH2:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]2[NH:32][N:33]=[N:34][N:35]=2)=[CH:23][CH:24]=1)[CH:36]([CH3:37])[CH3:38])([OH:39])=[O:8]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178447301HCID 178447301, compound

Product 1

HCID 178447302HCID 178447302, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 21.1 g (40 mmol) of N-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]-N-valeryl-(L)-valine benzyl ester in 210 ml of methanol is hydrogenated at room temperature with the addition of 4 g of Pd/C (10% ) until the calculated amount of hydrogen has been absorbed (24 hours). The crude acid is obtained by filtration and evaporation of the solution. It is partitioned between 80 ml of 2N potassium hydroxide solution and 50 ml of ether. The aqueous phase is separated off and rendered acidic, and the title compound is isolated by extraction with ethyl acetate. It is obtained from ethyl acetate in crystalline form and has a melting interval of 105°-1150° and an optical rotation [α]D20 of -69.95°±0.05° (c=1% in methanol).

Workup

  1. customhas been absorbed (24 hours)
  2. customThe crude acid is obtained by filtration and evaporation of the solution
  3. customIt is partitioned between 80 ml of 2N potassium hydroxide solution and 50 ml of ether
  4. customThe aqueous phase is separated off

Sources & evidence

ORD record
ord-591f4a7763f4428e98e4233c1bfa5da7
Source dataset
uspto-grants-1995_03
Patent number
US05399578

Reaction notes

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