2-[3(S)-(tert-butoxycarbonyl)amino-5(S)-(p-tert-butyl-benzyl)-2(S)-hydroxy-6-methyl-heptyl]-N-butyl-acrylamide → HCID 53839344, compound

HRID 725580Notes

Reaction equation

HRID 725580 reaction equation
[CH2:1]([NH:5][C:6](=[O:37])[C:7](=[CH2:36])[CH2:8][C@H:9]([OH:35])[C@@H:10]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:11][C@@H:12]([CH:24]([CH3:26])[CH3:25])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:16][CH:15]=1)[CH2:2][CH2:3][CH3:4]>O1CCCC1.[Pd]>[CH2:1]([NH:5][C:6](=[O:37])[CH:7]([CH3:36])[CH2:8][C@H:9]([OH:35])[C@@H:10]([NH:27][C:28]([O:30][C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29])[CH2:11][C@@H:12]([CH:24]([CH3:25])[CH3:26])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:16][CH:15]=1)[CH2:2][CH2:3][CH3:4]

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 53839344HCID 53839344, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

150 mg of N-tert-butoxycarbonyl-2-methylene-4(S)-hydroxy-5(S)-amino-7(S)-isopropyl-8-(p-tert-butyl-phenyl)-octanoic acid (N-butyl)amide (diastereoisomer I) are hydrogenated in the presence of 150 mg of 10% Pd/C in 20 ml of tetrahydrofuran for 2 hours at room temperature and under normal pressure. The reaction mixture is filtered and concentrated by evaporation. The residue is purified by means of FC (50 g of silica gel, dichloromethane/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 means of FC (50 g of silica gel, dichloromethane/diethyl ether=8:2)

Sources & evidence

ORD record
ord-bc49ebdc380b49e4a50c94883ed0c5a6
Source dataset
uspto-grants-1998_01
Patent number
US05705658

Reaction notes

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