HCID 70237630, compound → HCID 70204322, compound

HRID 651815Notes

Reaction equation

HRID 651815 reaction equation
[C:1]([O:5][C:6]([C@H:8]([C@@H:18]([CH2:31][CH:32]([CH3:34])[CH3:33])[C:19]([NH:21][N:22]1[C:27](=[O:28])[NH:26][C:25](=[O:29])[NH:24][C:23]1=[O:30])=[O:20])[CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)(=O)C.[Pt](=O)=O>[CH:12]1([CH2:11][CH2:10][CH2:9][C@@H:8]([C@@H:18]([CH2:31][CH:32]([CH3:34])[CH3:33])[C:19]([NH:21][N:22]2[C:27](=[O:28])[NH:26][C:25](=[O:29])[NH:24][C:23]2=[O:30])=[O:20])[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 1

HCID 70237630HCID 70237630, compound

Product 1

HCID 70204322HCID 70204322, compoundYield 25.5%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 0.500 g of 2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenylbutyl]-4-methyl-N-(2,4,6-trioxo-1,3,5-triazin-1-yl)valeramide (prepared as described in Example 44, part (i)) in 7 ml of glacial acetic acid was hydrogenated in the presence of 0.05 g of platinum (IV) oxide for 1.5 hours. Filtration and evaporation gave a residue which was purified by flash column chromatography on silica gel using ethyl acetate/hexane (1:1) as the eluant to give 0.129 g of 2(R)-[4-cyclohexyl-1(S)-(tert-butoxycarbonyl)butyl]-N-(2,4,6-trioxo-1,3,5-triazin-1-yl)-4-methylvaleramide in the form of a white solid.

Workup

  1. filtrationFiltration and evaporation
  2. customgave a residue which
  3. customwas purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-762ae3525baf40c295fe341fec2416fe
Source dataset
uspto-grants-2001_08
Patent number
US06281363B1

Reaction notes

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