HCID 10258691, compound → Cgs 25462

HRID 487227Notes

Reaction equation

HRID 487227 reaction equation
[C:1]1([O:7][P:8]([CH2:17][NH:18][C@@H:19]([CH2:35][C:36]2[CH:41]=[CH:40][C:39]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[CH:38][CH:37]=2)[C:20]([NH:22][CH2:23][CH2:24][C:25]([O:27]CC2C=CC=CC=2)=[O:26])=[O:21])([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(OCC)(=O)C.[Pd]>[C:1]1([O:7][P:8]([CH2:17][NH:18][C@@H:19]([CH2:35][C:36]2[CH:37]=[CH:38][C:39]([C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)=[CH:40][CH:41]=2)[C:20]([NH:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[O:21])([O:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 10258691HCID 10258691, compound

Product 1

HCID 132812Cgs 25462

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of benzyl (S)-N-[2-(diphenylphosphonomethylamino)-3-(4-biphenylyl)-propionyl]-3-aminopropionate (1.8 g. 2.77 mmol) in ethyl acetate (30 mL) is hydrogenated in a Parr shaker in the presence of palladium on carbon (10%, 800 mg) at 40 psi for 4 hours. The catalyst is filtered off and washed with methanol (30 mL). After concentration of the filtrate in vacuo, the residue is triturated with ether and the resulting crystalline solid dried under reduced pressure to give (S)-N-[2-(diphenylphosphonomethylamino)-3-(4-biphenylyl)propionyl]-3-aminopropionic acid. It is recrystallized to constant melting point from methanol/ether, m.p. 102°; [α]D =-8.99 (c=0.95, CH3OH).

Workup

  1. filtrationThe catalyst is filtered off
  2. washwashed with methanol (30 mL)
  3. customAfter concentration of the filtrate in vacuo, the residue is triturated with ether
  4. customthe resulting crystalline solid dried under reduced pressure

Sources & evidence

ORD record
ord-b8082d057ea940b798a0dce8e8bba946
Source dataset
uspto-grants-1994_03
Patent number
US05294632

Reaction notes

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