HCID 131713508, compound → HCID 53879827, compound

HRID 638167Notes

Reaction equation

HRID 638167 reaction equation
[CH2:1]([N:3]([CH2:21][P:22]([O:34][CH2:35][O:36][C:37](=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39])([CH2:24][CH2:25][CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:23])[C:4]([N:6]1[CH2:20][CH2:19][CH2:18][C@H:7]1[C:8]([O:10]CC1C=CC=CC=1)=[O:9])=[O:5])[CH3:2]>CO.[Pd]>[CH2:1]([N:3]([CH2:21][P:22]([O:34][CH2:35][O:36][C:37](=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39])([CH2:24][CH2:25][CH2:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:23])[C:4]([N:6]1[CH2:20][CH2:19][CH2:18][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 131713508HCID 131713508, compound

Product 1

HCID 53879827HCID 53879827, 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-[[ethyl[[[(2,2-dimethyl-1-oxopropoxy)methoxy](4-phenylbutyl)phosphinyl]methyl]amino]carbonyl]-L-proline.

Workup

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

Sources & evidence

ORD record
ord-6be1968821fb439fa8a528c3275bd714
Source dataset
uspto-grants-1985_12
Patent number
US04560681

Reaction notes

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