Benzyl 3-(2-propionyloxy-5-(ethoxy(diethylphosphonomethyl)phosphinoyl)phenyl)-3-methylbutanoate → HCID 86655578, compound

HRID 39279Notes

Reaction equation

HRID 39279 reaction equation
[C:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([P:12]([O:23][CH2:24][CH3:25])([CH2:14][P:15]([O:20][CH2:21][CH3:22])([O:17][CH2:18][CH3:19])=[O:16])=[O:13])=[CH:8][C:7]=1[C:26]([CH3:39])([CH3:38])[CH2:27][C:28]([O:30]CC1C=CC=CC=1)=[O:29])(=[O:4])[CH2:2][CH3:3]>CO.[Pd]>[C:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([P:12]([O:23][CH2:24][CH3:25])([CH2:14][P:15]([O:17][CH2:18][CH3:19])([O:20][CH2:21][CH3:22])=[O:16])=[O:13])=[CH:8][C:7]=1[C:26]([CH3:39])([CH3:38])[CH2:27][C:28]([OH:30])=[O:29])(=[O:4])[CH2:2][CH3:3]

Participants

4

Reactant 1

HCID 86655577Benzyl 3-(2-propionyloxy-5-(ethoxy(diethylphosphonomethyl)phosphinoyl)phenyl)-3-methylbutanoate

Product 1

HCID 86655578HCID 86655578, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Compound 123 (300 mg, 0.515 mmol) was dissolved in methanol (5 mL) and hydrogenated over Pd/C (30%, 95 mg) under H2 (1 atm) for 3 hr. The catalyst was filtered off and the solvent removed under reduced pressure resulting in the pale-yellow liquid 124 (234 mg, 92%): 1H NMR (400 MHz, CDCl3) δ 1.21 (t, J=7.0, 3H), 1.25 (m, 9H), 1.49 (s, 3H), 1.52 (s, 3H), 2.55-2.68 (m, 4H), 2.72 (AB q, J=13.8, 2H), 3.90-4.13 (m, 6H), 7.15 (dd, J=3.5, 8.1, 1H), 7.67 (ddd, J=1.8, 8.3, 11.8, 1H), 7.84 (dd, J=1.8, 13.7, 1H): 31P (162 MHz, CDCl3) δ 17.53 (d, J=3.7, 1P), 31.82 (d, J=3.7, 1P).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-b282074ad22e4db2a85b4574fd35bb3e
Source dataset
uspto-grants-2013_09
Patent number
US08524691B2

Reaction notes

Loading…