HCID 131713403, compound → HCID 54536247, compound

HRID 1388748Notes

Reaction equation

HRID 1388748 reaction equation
[CH2:1]([O:3][P:4]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([NH:6][C@H:7]([C:9]([N:11]1[CH2:25][CH2:24][CH2:23][C@H:12]1[C:13]([O:15]CC1C=CC=CC=1)=[O:14])=[O:10])[CH3:8])=[O:5])[CH3:2]>[C].[Pd].CO>[CH2:1]([O:3][P:4]([CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)([NH:6][C@H:7]([C:9]([N:11]1[CH2:25][CH2:24][CH2:23][C@H:12]1[C:13]([OH:15])=[O:14])=[O:10])[CH3:8])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 131713403HCID 131713403, compound

Product 1

HCID 54536247HCID 54536247, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A solution of the ester product from part (b) (1.42 g., 3.1 mmole) in 60 ml. of methanol is treated with 10% palladium-carbon catalyst (350 mg.) and hydrogenated in a Parr apparatus at an initial pressure of 45 psi. for 1.5 hours. The mixture is filtered through Celite and evaporated to dryness to give 1-[N-[ethoxy(phenylmethyl)phosphinyl]-L-alanyl]-L-proline as a colorless foam. Tlc (10% methanoldichloromethane) shows a single spot at Rf 0.31.

Workup

  1. filtrationThe mixture is filtered through Celite
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-244af5e9f65a4201afa88daf66ab2130
Source dataset
uspto-grants-1984_02
Patent number
US04432971

Reaction notes

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