2-[3(S)-(tert-butoxycarbonyl)amino-5(S)-(p-tert-butyl-benzyl)-2(S)-hydroxy-6-methyl-heptyl]-N-butyl-acrylamide → 5(S)-(tert-butoxycarbonyl)amino7(S)-(p-tert-butyl-benzyl)-4(S)-hydroxy-2(R,S),8-dimethyl-nonanoic acid N-(butyl)amide

HRID 2258300Notes

Reaction equation

HRID 2258300 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:22][C@H:23]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:30][CH:29]=1)[CH:24]([CH3:26])[CH3:25])[C@@H:10]([OH:21])[CH2:11][C:12](=[CH2:20])[C:13]([NH:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2]>O1CCCC1.[Pd]>[CH2:16]([NH:15][C:13](=[O:14])[CH:12]([CH3:20])[CH2:11][C@H:10]([OH:21])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:22][C@H:23]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]([CH3:37])([CH3:35])[CH3:36])=[CH:30][CH:29]=1)[CH:24]([CH3:26])[CH3:25])[CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 1

HCID 545017412-[3(S)-(tert-butoxycarbonyl)amino-5(S)-(p-tert-butyl-benzyl)-2(S)-hydroxy-6-methyl-heptyl]-N-butyl-acrylamide

Product 1

HCID 538393445(S)-(tert-butoxycarbonyl)amino7(S)-(p-tert-butyl-benzyl)-4(S)-hydroxy-2(R,S),8-dimethyl-nonanoic acid N-(butyl)amide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

150 mg of 2-[3(S)-(tert-butoxycarbonyl)amino-5(S)-(p-tert-butyl-benzyl)-2(S)-hydroxy-6-methyl-heptyl]-N-butyl-acrylamide (diastereoisomer I, Application Example 2b) are hydrogenated in the presence of 150 mg of 10% Pd/C in tetrahydrofuran (20 ml) for 2 hours at room temperature and under normal pressure. The reaction mixture is filtered and concentrated by evaporation. The residue is purified by FC (50 g of silica gel, dichloro-methane/diethyl ether 8:2). The title compound is obtained in the form of a diastereoisomeric mixture: Rf (dichloromethane/diethyl ether 8:2)=0.18.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationconcentrated by evaporation
  3. customThe residue is purified by FC (50 g of silica gel, dichloro-methane/diethyl ether 8:2)

Sources & evidence

ORD record
ord-1689cc099e044d688f2e46ae80fdd078
Source dataset
uspto-grants-1997_08
Patent number
US05659065

Reaction notes

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