HCID 131719572, compound → HCID 66691394, compound

HRID 744802Notes

Reaction equation

HRID 744802 reaction equation
[CH2:1]([NH:5][C:6](=[O:44])[C@H:7]([CH:41]([CH3:43])[CH3:42])[CH2:8][C@H:9]([OH:40])[C@@H:10]([N:37]=[N+]=[N-])[CH2:11][C@@H:12]([CH:34]([CH3:36])[CH3:35])[CH:13](OC(=O)C(C)C)[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.[Pd]>[CH2:1]([NH:5][C:6](=[O:44])[C@H:7]([CH:41]([CH3:43])[CH3:42])[CH2:8][C@H:9]([OH:40])[C@@H:10]([NH2:37])[CH2:11][C@@H:12]([CH:34]([CH3:35])[CH3:36])[CH2:13][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 131719572HCID 131719572, compound

Product 1

HCID 66691394HCID 66691394, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

50 mg of 5(S)-azido-4(S)-hydroxy-8(R,S)-isobutyroxy-2(S),7(S)-diisopropyl-8-[4-methoxy-3-(2-methoxymethoxyethyl)-phenyl]-octanoic acid (N-butyl)amide are hydrogenated in 10 ml of methanol in the presence of 50 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 means of FC (2 g of silica gel, dichloromethane/methanol=9:1). The title compound is obtained: Rf (dichloromethane/methanol=9:1)=0.19; HPLC Rt =13.42 minutes; FAB-MS (M+H)+ =509.

Workup

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

Sources & evidence

ORD record
ord-510ff4973f17483f913e924ddb33b848
Source dataset
uspto-grants-1996_09
Patent number
US05559111

Reaction notes

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