HCID 131719572, compound → HCID 66691394, compound

HRID 1452117Notes

Reaction equation

HRID 1452117 reaction equation
[N:1]([C@H:4]([C@@H:31]([OH:44])[CH2:32][C@H:33]([C:37](=[O:43])[NH:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH:34]([CH3:36])[CH3:35])[CH2:5][C@@H:6]([CH:28]([CH3:30])[CH3:29])[CH:7](OC(=O)C(C)C)[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([CH2:16][CH2:17][O:18][CH2:19][O:20][CH3:21])[CH:9]=1)=[N+]=[N-]>CO.[Pd]>[CH2:39]([NH:38][C:37](=[O:43])[C@H:33]([CH:34]([CH3:36])[CH3:35])[CH2:32][C@H:31]([OH:44])[C@@H:4]([NH2:1])[CH2:5][C@H:6]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([CH2:16][CH2:17][O:18][CH2:19][O:20][CH3:21])[CH:9]=1)[CH:28]([CH3:29])[CH3:30])[CH2:40][CH2:41][CH3:42]

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 {4(S)-Azido-7(S)-butylcarbamoyl-5(S)-hydroxy-2(S)-isopropyl-8-methyl-1 (R,S)-[4- methoxy-3-(2-methoxymethoxyethyl)-phenyl]-nonyl}-isobutyrate are hydrogenated in 10 ml of methanol in the presence of 50 mg of 10% Pd/C at room temperature and normal pressure. The reaction mixture is filtered and concentrated by evaporation. The residue is purified by 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 FC (2 g of silica gel, dichloromethane/methanol 9:1)

Sources & evidence

ORD record
ord-6f4f095fe6d64f8abb591c3f8cc19f66
Source dataset
uspto-grants-1997_02
Patent number
US05606078

Reaction notes

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