HCID 68767905, compound → HCID 68767644, compound

HRID 1170419Notes

Reaction equation

HRID 1170419 reaction equation
[C:1]([O:5][C:6](=[O:43])[NH:7][C@:8]([CH2:29][O:30][P:31]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])([CH3:28])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17]CC2C=CC=CC=2)=[C:13]([N+:25]([O-])=O)[CH:12]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:43])[NH:7][C@:8]([CH2:29][O:30][P:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:32])([CH3:28])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([NH2:25])[CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 68767905HCID 68767905, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68767644HCID 68767644, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Under an atmosphere of argon, a solution of [(R)-3-(4-Benzyloxy-3-nitro-phenyl)-1-(di-tert-butoxy-phosphoryloxymethyl)-1-methyl-propyl]-carbamic acid tert-butyl ester (5.36 g, 8.6 mmol) in ethanol (250 mL) was treated with 10% palladium on charcoal (1.22 g). Argon was replaced by hydrogen and the reaction was stirred for 16 hours at RT. After filtration and removal of the solvent in vacuum, the residue was purified by silica gel column chromatography (dichloromethane/methanol 10/1) yielding the title compound as a colorless solid. 1H-NMR (CD3OD): δ=6.61-6.57 (m; 2H), 6.41 (dd; 1H), 6.22 (s; 1H), 4.55 (s; 1H), 4.41/3.93 (2m; 2H), 2.43 (m; 1H), 2.05 (m; 1H), 1.70 (m; 1H), 1.48 (s; 18H), 1.44 (s; 9H), 1.28 (s; 3H); MS (ESI+): 503.4 [M+H]+

Workup

  1. filtrationAfter filtration and removal of the solvent in vacuum
  2. customthe residue was purified by silica gel column chromatography (dichloromethane/methanol 10/1)

Sources & evidence

ORD record
ord-879383a9164f4809aa06f3dc3dbde2dc
Source dataset
uspto-grants-2010_11
Patent number
US07825260B2

Reaction notes

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