Triethylamine → HCID 23625640, compound

HRID 744792Notes

Reaction equation

HRID 744792 reaction equation
[CH2:1]([NH:5][C:6](=[O:43])[C:7](=[CH2:42])[CH2:8][C@H:9]([OH:41])[C@@H:10]([NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:11][C@@H:12]([CH:30]([CH3:32])[CH3:31])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:15]=1)[CH2:2][CH2:3][CH3:4].CCN(CC)CC>CO>[CH2:1]([NH:5][C:6](=[O:43])[C@H:7]([CH3:42])[CH2:8][C@H:9]([OH:41])[C@@H:10]([NH:33][C:34]([O:36][C:37]([CH3:38])([CH3:40])[CH3:39])=[O:35])[CH2:11][C@@H:12]([CH:30]([CH3:31])[CH3:32])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:15]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 23625182HCID 23625182, compound

Product 1

HCID 23625640HCID 23625640, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.5 g of N-tert-butoxycarbonyl-2-methylene-4(S)-hydroxy-5(S)-amino-7(S)-isopropyl-8-(3-benzyloxy-4-methoxy-phenyl)-octanoic acid (N-butyl)amide are hydrogenated in 30 ml of absolute methanol 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 the filtrate is concentrated by evaporation. The residue is purified by FC (200 g of silica gel, hexane/ethyl acetate=1:1). Title compound: Rf (hexane/ethyl acetate=1:1)=0.16; FAB-MS (M+H)+ =599.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated by evaporation
  3. customThe residue is purified by FC (200 g of silica gel, hexane/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-5cdac818aef04b9287170460de23ee18
Source dataset
uspto-grants-1996_09
Patent number
US05559111

Reaction notes

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