benzyl 2(RS)-[[(RS)-(ethoxy)[(2,5-dioxo-1-imidazolidinyl)methyl]phosphinyl]methyl]-4-methylvalerate → 2(RS)-[[(RS)-(ethoxy)[(2,5-dioxo-1-imidazolidinyl)-methyl]phosphinyl]methyl]-4-methylvaleric acid

HRID 476721Notes

Reaction equation

HRID 476721 reaction equation
[CH2:1]([O:3][P:4]([CH2:14][CH:15]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:16]([O:18]CC1C=CC=CC=1)=[O:17])([CH2:6][N:7]1[C:11](=[O:12])[CH2:10][NH:9][C:8]1=[O:13])=[O:5])[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][P:4]([CH2:14][CH:15]([CH2:26][CH:27]([CH3:28])[CH3:29])[C:16]([OH:18])=[O:17])([CH2:6][N:7]1[C:11](=[O:12])[CH2:10][NH:9][C:8]1=[O:13])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 20062992benzyl 2(RS)-[[(RS)-(ethoxy)[(2,5-dioxo-1-imidazolidinyl)methyl]phosphinyl]methyl]-4-methylvalerate

Product 1

HCID 200630052(RS)-[[(RS)-(ethoxy)[(2,5-dioxo-1-imidazolidinyl)-methyl]phosphinyl]methyl]-4-methylvaleric acidYield 102.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

0.27 g (0.64 mmol) of benzyl 2(RS)-[[(RS)-(ethoxy)[(2,5-dioxo-1-imidazolidinyl)methyl]phosphinyl]methyl]-4-methylvalerate was dissolved in 10 ml of ethanol and the solution was hydrogenated in the presence of 0.2 g of 10% palladium/carbon at room temperature and under atmospheric pressure. After 1 hour, the catalyst was removed by filtration and the solvent was evaporated to give 0.22 g of 2(RS)-[[(RS)-(ethoxy)[(2,5-dioxo-1-imidazolidinyl)methyl]phosphinyl]methyl]-4-methylvaleric acid in the form of a foam;

Workup

  1. customthe catalyst was removed by filtration
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-46d8cee60a3c4c95abdda6c78a1fc66a
Source dataset
uspto-grants-1989_12
Patent number
US04885283

Reaction notes

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