Reaction #1904051

ord-96042dcb429c4efca87328da29667665

Reaction equation

COP(=O)(C[C@@H](NC(=O)OCc1ccccc1)C(=O)Nc1ccc(N2CCOCC2=O)cc1)OC
(S)-2-(benzyloxycarbonyl-amino)-N-[4-(3-oxomorpholin-4-yl)phenyl]-3-(dimethoxyphosphoryl)-propionamide
[H][H]
hydrogen
→
COP(=O)(C[C@@H](N)C(=O)Nc1ccc(N2CCOCC2=O)cc1)OC
(S)-2-amino-N-[4-(3-oxomorpholin-4-yl)phenyl]-3-(dimethoxyphosphoryl)propionamide
Yield 93.2%

Reactants

COP(=O)(C[C@@H](NC(=O)OCc1ccccc1)C(=O)Nc1ccc(N2CCOCC2=O)cc1)OC
(S)-2-(benzyloxycarbonyl-amino)-N-[4-(3-oxomorpholin-4-yl)phenyl]-3-(dimethoxyphosphoryl)-propionamide
[H][H]
hydrogen

Reagents

[Pd]
palladium/carbon

Solvents

CO
methanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    FiltrationThe reaction mixture is subsequently filtered off
  2. 2
    Otherthe filtrate is evaporated to dryness

Procedure

5.3 The mixture of 0.39 g (0.78 mmol) of (S)-2-(benzyloxycarbonyl-amino)-N-[4-(3-oxomorpholin-4-yl)phenyl]-3-(dimethoxyphosphoryl)-propionamide and 0.4 g of 5% palladium/carbon in 30 ml of methanol is hydrogenated until hydrogen is no longer taken up. The reaction mixture is subsequently filtered off, and the filtrate is evaporated to dryness, giving 0.27 g of (S)-2-amino-N-[4-(3-oxomorpholin-4-yl)phenyl]-3-(dimethoxyphosphoryl)propionamide as colourless oil, ESI 371.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07598241B2uspto-grants-2009_10