HCID 131720007, compound → HCID 131720006, compound

HRID 2256772Notes

Reaction equation

HRID 2256772 reaction equation
[CH2:1]([NH:5][C:6](=[O:39])[C@H:7]([CH:36]([CH3:38])[CH3:37])[CH2:8][C@H:9]([OH:35])[C@@H:10]([N:32]=[N+]=[N-])[CH2:11][C@@H:12]([CH:29]([CH3:31])[CH3:30])[CH:13]([OH:28])[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([CH2:22][CH2:23][O:24][CH2:25][O:26][CH3:27])[CH:15]=1)[CH2:2][CH2:3][CH3:4]>CO.C(O)(=O)C.[Pd]>[CH2:1]([NH:5][C:6](=[O:39])[C@H:7]([CH:36]([CH3:38])[CH3:37])[CH2:8][C@H:9]([OH:35])[C@@H:10]([NH2:32])[CH2:11][C@@H:12]([CH:29]([CH3:30])[CH3:31])[CH:13]([OH:28])[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([CH2:22][CH2:23][O:24][CH2:25][O:26][CH3:27])[CH:15]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 131720007HCID 131720007, compound

Product 1

HCID 131720006HCID 131720006, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 10129899Acetic acid methanolSolvent

Procedure

40 mg of 5(S)-azido-4(S),8(R,S)-dihydroxy-2(S),7(S)-diisopropyl-8-[4-methoxy-3-(2-methoxymethoxyethyl)-phenyl]-octanoic acid (N-butyl)-amide are hydrogenated in 10 ml of methanol/acetic acid (9:1) in the presence of 20 mg of 10% Pd/C at room temperature and under normal pressure. The reaction mixture is filtered and concentrated by evaporation. The residue is purified by FC (2.4 g of silica gel, dichloromethane/methanol=9:1). The title compound is obtained: Rf (dichloromethane/methanol=9:1)=0.17; HPLC Rt =11.44 and 12.63 minutes (diastereoisomeric mixture); FAB-MS (M+H)+ =525.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationconcentrated by evaporation
  3. customThe residue is purified by FC (2.4 g of silica gel, dichloromethane/methanol=9:1)

Sources & evidence

ORD record
ord-9e9a43931a54466b9dfc3e3790131a68
Source dataset
uspto-grants-1997_08
Patent number
US05654445

Reaction notes

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