HCID 131714446, compound → HCID 70442474, compound

HRID 986777Notes

Reaction equation

HRID 986777 reaction equation
[C:1]([NH:9][CH:10]([CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[CH2:11][P:12]([CH2:23][C:24]([N:26]1[CH2:40][CH2:39][CH2:38][C@H:27]1[C:28]([O:30]CC1C=CC=CC=1)=[O:29])=[O:25])([O:14][CH2:15][O:16][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Pd]>[C:1]([NH:9][CH:10]([CH2:41][C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)[CH2:11][P:12]([CH2:23][C:24]([N:26]1[CH2:40][CH2:39][CH2:38][C@H:27]1[C:28]([OH:30])=[O:29])=[O:25])([O:14][CH2:15][O:16][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 131714446HCID 131714446, compound

Product 1

HCID 70442474HCID 70442474, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of the diester product from part (a) in methanol is added to a 10% palladium on carbon catalyst and the resulting mixture is shaken in a Parr hydrogenation apparatus for several hours. The catalyst is filtered off and the methanol is stripped from the filtrate. The crude product is chromatographed on silica gel to yield (S)-1-[[[2-(benzoylamino)-3-phenylpropyl][(2,2-dimethyl-1-oxopropoxy)methoxy]phosphinyl]acetyl]-L-proline.

Workup

  1. filtrationThe catalyst is filtered off
  2. customThe crude product is chromatographed on silica gel

Sources & evidence

ORD record
ord-c7db24fc4f68429a86eea67f1e3a26fc
Source dataset
uspto-grants-1987_12
Patent number
US04716155

Reaction notes

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