HCID 23625182, compound → HCID 23625640, compound

HRID 2258301Notes

Reaction equation

HRID 2258301 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]([O:34][CH3:35])=[C:30]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[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]>CO>[CH2:16]([NH:15][C:13](=[O:14])[C@H: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]([O:34][CH3:35])=[C:30]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:29]=1)[CH:24]([CH3:25])[CH3:26])[CH2:17][CH2:18][CH3:19]

Participants

3

Reactant 1

HCID 23625182HCID 23625182, compound

Product 1

HCID 23625640HCID 23625640, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-[3(S)-(tert-butoxycarbonyl)amino-5(S)-(3-benzyloxy-4-methoxy-benzyl)-2(S)-hydroxy-6-methyl-heptyl]-N-butyl-acrylamide (3.5 g) in absolute methanol (30 ml) is hydrogenated under an inert atmosphere in the presence of 20 mg of [Ru2Cl4 ((S)-BINAP)2 ]·NEt3 at room temperature and 25 bar for 5 hours. The reaction mixture is filtered and after concentration of the filtrate the residue is purified by FC (200 g of silica gel, hexane/ethyl acetate 1:1). The title compound is obtained: Rf (hexane/ethyl acetate 1:1)=0.16; FAB-MS (M+H)+ =599.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customafter concentration of the filtrate the residue is purified by FC (200 g of silica gel, hexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-0f49fbaa38c541b49d7fa1d648cfd9c3
Source dataset
uspto-grants-1997_08
Patent number
US05659065

Reaction notes

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