2-[[(Ethoxy)(phthalimidomethyl)phosphinyl]methyl]-4-methylvalerate → 2-[[(Ethoxy)(phthalimidomethyl)phosphinyl]methyl]-4-methylvaleric acid

HRID 1085016Notes

Reaction equation

HRID 1085016 reaction equation
[CH2:1]([O:3][P:4]([CH2:18][CH:19]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:20]([O-:22])=[O:21])([CH2:6][N:7]1[C:11](=[O:12])[C:10]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:9]2[C:8]1=[O:17])=[O:5])[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][P:4]([CH2:18][CH:19]([CH2:23][CH:24]([CH3:25])[CH3:26])[C:20]([OH:22])=[O:21])([CH2:6][N:7]1[C:8](=[O:17])[C:9]2=[CH:16][CH:15]=[CH:14][CH:13]=[C:10]2[C:11]1=[O:12])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 867435622-[[(Ethoxy)(phthalimidomethyl)phosphinyl]methyl]-4-methylvalerate

Product 1

HCID 200630162-[[(Ethoxy)(phthalimidomethyl)phosphinyl]methyl]-4-methylvaleric acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4.5 g of benzyl (R or S)-2-[[(ethoxy)(phthalimidomethyl)phosphinyl]methyl]-4-methylvalerate were dissolved in 120 ml of ethanol and the solution was hydrogenated over 1.6 g of 10% palladium-on-charcoal for 5.5 hours. After filtration and evaporation of the filtrate, there were obtained 3.0 g of (R or S)-2-[[(ethoxy)(phthalimidomethyl)phosphinyl]methyl]-4-methylvaleric acid in the form of a white foam.

Workup

  1. filtrationAfter filtration and evaporation of the filtrate

Sources & evidence

ORD record
ord-b8c93bd84f20418cb0e639289bf6cf6e
Source dataset
uspto-grants-1991_04
Patent number
US05006651

Reaction notes

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