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 490944Notes

Reaction equation

HRID 490944 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:16]([CH2:21][P:22]([CH:27]([NH:31]C(OCC2C=CC=CC=2)=O)[CH:28]([CH3:30])[CH3:29])([O:24][CH2:25][CH3:26])=[O:23])[C:17]([O:19][CH3:20])=[O:18])[CH:13]=[CH:14][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[CH3:20][O:19][C:17](=[O:18])[CH:16]([C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([CH2:9][NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH:11]=1)[CH2:21][P:22]([CH:27]([NH2:31])[CH:28]([CH3:29])[CH3:30])([O:24][CH2:25][CH3:26])=[O:23]

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), 2.00-2.90 (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-cdc16a4339274f429f77c1bef35924d0
Source dataset
uspto-grants-2009_05
Patent number
US07528173B2

Reaction notes

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