2-(3-(t-Butoxycarbonylamino)methylphenyl)-3-((1-(benzyloxycarbonyl)amino-2-methylpropyl)(ethoxy)phosphinoyl)propanoic acid methyl ester → 2-(3-(t-Butoxycarbonylamino)methylphenyl)-3-((1-amino-2-methylpropyl)(ethoxy)-phosphinoyl)propanoic acid methyl ester

HRID 1677623Notes

Reaction equation

HRID 1677623 reaction equation
[CH3:1][O:2][C:3](=[O:41])[CH:4]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32][NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH:27]=1)[CH2:5][P:6]([CH:11]([NH:15]C(OCC1C=CC=CC=1)=O)[CH:12]([CH3:14])[CH3:13])([O:8][CH2:9][CH3:10])=[O:7]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:41])[CH:4]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32][NH:33][C:34]([O:36][C:37]([CH3:39])([CH3:38])[CH3:40])=[O:35])[CH:27]=1)[CH2:5][P:6]([CH:11]([NH2:15])[CH:12]([CH3:13])[CH3:14])([O:8][CH2:9][CH3:10])=[O:7]

Participants

4

Reactant 1

HCID 673761572-(3-(t-Butoxycarbonylamino)methylphenyl)-3-((1-(benzyloxycarbonyl)amino-2-methylpropyl)(ethoxy)phosphinoyl)propanoic acid methyl ester

Product 1

HCID 673750552-(3-(t-Butoxycarbonylamino)methylphenyl)-3-((1-amino-2-methylpropyl)(ethoxy)-phosphinoyl)propanoic acid methyl esterYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-(3-(t-butoxycarbonylamino)methylphenyl)-3-((1-(benzyloxycarbonyl)amino-2-methylpropyl)(ethoxy)phosphinoyl)propanoic acid methyl ester (10.6 g, 18.0 mmol) in 200 mL methanol was added Pd/C (10%) (2.1 g). The reaction mixture was hydrogenated in H2 (50 psi) for 2 to 3 hours. The catalyst was filtered over a celite pad. The solvent was removed in vacuo to afford 2-(3-(t-butoxycarbonylamino)methylphenyl)-3-((1-amino-2-methylpropyl)(ethoxy)-phosphinoyl)propanoic acid methyl ester (7.1 g, 15.6 mmol, 87%) as white solid, NMR (DMSO-d6) 0.80-0.91 (m, 6), 1.05-1.18 (m, 3), 1.37 (s, 9), 1.46 (m, 1), 1.90 (m, 1), 2.00-2.20 (m, 1), 2.56-2.64 (m, 1), 3.56 (s, 3), 3.70-3.95 (m, 3), 4.08 (d, 2), 7.10-7.20 (3, m), 7.24 (m, 1), 7.38 (t, 1) ppm.

Workup

  1. filtrationThe catalyst was filtered over a celite pad
  2. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-317522cec6294952b274bb1fd5f1a1c1
Source dataset
uspto-grants-2011_08
Patent number
US08008325B2

Reaction notes

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