Magnesium → HCID 86756919, compound

HRID 1979222Notes

Reaction equation

HRID 1979222 reaction equation
[C:1]([O:5][C:6]([C@H:8]([C@@H:18]([CH2:38][CH:39]([CH3:41])[CH3:40])[C:19]([NH:21][N:22]([CH2:33][C@@H:34]([CH3:37])[CH2:35][CH3:36])S(C1C=CC(C)=CC=1)(=O)=O)=[O:20])[CH2:9]/[CH:10]=[CH:11]/[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Mg]>>[C:1]([O:5][C:6]([C@H:8]([C@@H:18]([CH2:38][CH:39]([CH3:40])[CH3:41])[C:19]([NH:21][NH:22][CH2:33][C@@H:34]([CH3:37])[CH2:35][CH3:36])=[O:20])[CH2:9]/[CH:10]=[CH:11]/[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

3

Reactant 2

HCID 5462224MagnesiumHCID 86756917HCID 86756917, compound

Product 1

HCID 86756919HCID 86756919, compoundYield 61%

Procedure

A mixture of 0.325 g of (E)-2(R)-[1(S)-(tert.-butoxycarbonyl)-4-phenyl-3-butenyl)-4-methyl-2′-(2(S)-methylbutyl)-2′-(p-toluenesulphonyl)valerohydrazide and 0.135 g of magnesium powder was placed in a sonic bath for 1.5 hours. The methanol was evaporated and the residue was partitioned between diethyl ether and potassium hydrogen sulphate solution. The ethereal layer was washed in sequence with potassium hydrogen sulphate solution, 5% sodium hydrogen carbonate solution, water and saturated sodium chloride solution, dried over anhydrous magnesium sulphate and evaporated. The residue was purified by flash chromatography on silica gel using hexane/ethyl acetate (5:1) for the elution. There was obtained 0.146 g of (E)-2(R)-[1(S)-(tert.-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methyl-2′-(2(S)-methylbutyl)valerohydrazide in the form of a white solid.

Workup

  1. customThe methanol was evaporated
  2. customthe residue was partitioned between diethyl ether and potassium hydrogen sulphate solution
  3. washThe ethereal layer was washed in sequence with potassium hydrogen sulphate solution, 5% sodium hydrogen carbonate solution, water and saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel
  7. washfor the elution

Sources & evidence

ORD record
ord-e028f1dd05364e90a9df2430eeaa14bf
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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