Methanol → HCID 53890036, compound

HRID 638164Notes

Reaction equation

HRID 638164 reaction equation
[CH2:1]([N:3]([CH2:21][P:22]([O:34][CH2:35][CH3:36])([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].ClCCl.CO.C(O)(=O)C>[CH2:1]([N:3]([CH2:21][P:22]([O:34][CH2:35][CH3:36])([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]([OH:10])=[O:9])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 887MethanolHCID 131714466HCID 131714466, compound

Product 1

HCID 53890036HCID 53890036, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21877243DCM MeOH AcOHSolvent

Procedure

A mixture of 1-[[ethyl[[ethoxy(4-phenylbutyl)phosphinyl]methyl]amino]carbonyl]-L-proline, phenylmethyl ester (800 mg., 1.56 mmole), methanol (50 ml.), and 10% palladium on carbon catalyst (150 mg.) was hydrogenated on the Parr apparatus at 50 psi for 1.5 hours. The catalyst was removed by filtration (Celite bed) and the methanol stripped to give 600 mg. residue. This residue was passed through a pad of silica eluting with dichloromethane/methanol/acetic acid (100/5/5) to remove a polar impurity. After evaporation and azeotropic removal (toluene) of residual acetic acid, 550 mg. of 1-[[ethyl[[ethoxy(4-phenylbutyl)phosphinyl]methyl]amino]carbonyl]-L-proline was obtained as an oil. Tlc (dichloromethane/methanol/acetic acid; 100:5:5) single spot at Rf =0.6.

Workup

  1. customThe catalyst was removed by filtration (Celite bed)
  2. customto give 600 mg
  3. customto remove a polar impurity
  4. customAfter evaporation and azeotropic removal (toluene) of residual acetic acid, 550 mg

Sources & evidence

ORD record
ord-92b2582b643e4905a5fe9f345164b625
Source dataset
uspto-grants-1985_12
Patent number
US04560681

Reaction notes

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