HCID 131712966, compound → HCID 22822619, compound

HRID 1649398Notes

Reaction equation

HRID 1649398 reaction equation
[C:1]([NH:9][CH:10]([P:20]([CH2:31][C:32]([N:34]1[CH2:48][CH2:47][CH2:46][C@H:35]1[C:36]([O:38]CC1C=CC=CC=1)=[O:37])=[O:33])([O:22][CH2:23][O:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])=[O:21])[CH2:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Pd]>[C:1]([NH:9][CH:10]([P:20]([CH2:31][C:32]([N:34]1[CH2:48][CH2:47][CH2:46][C@H:35]1[C:36]([OH:38])=[O:37])=[O:33])([O:22][CH2:23][O:24][C:25](=[O:30])[C:26]([CH3:28])([CH3:29])[CH3:27])=[O:21])[CH2:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 131712966HCID 131712966, compound

Product 1

HCID 22822619HCID 22822619, 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 (±)-1-[[[1-(benzoylamino)-4-phenylbutyl][(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-b7164e16ddd242d4b675b60b7e6df1eb
Source dataset
uspto-grants-1983_11
Patent number
US04416831

Reaction notes

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