Potassium Carbonate → HCID 86756917, compound

HRID 1979221Notes

Reaction equation

HRID 1979221 reaction equation
[C:1]([O:5][C:6]([C@H:8]([C@@H:18]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:19]([NH:21][NH:22][S:23]([C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=1)(=[O:25])=[O:24])=[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].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]([O:5][C:6]([C@H:8]([C@@H:18]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:19]([NH:21][N:22]([CH2:6][C@@H:8]([CH3:18])[CH2:9][CH3:10])[S:23]([C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=1)(=[O:25])=[O:24])=[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]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86756918HCID 86756918, compound

Product 1

HCID 86756917HCID 86756917, compoundYield 101.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.323 g of (E)-2(R)-[1(S)-(tert.-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methyl-2′-(p-toluenesulphonyl)valerohydrazide, 0.111 g of S(+)-1-bromo-2-methylbutane and 0.053 g of anhydrous potassium carbonate in 5 ml of dry dimethylformamide was stirred at room temperature overnight. The solvent was evaporated and the residue was partitioned between ethyl acetate and water. The ethyl acetate layer was washed with 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 0.187 g of (E)-2(R)-[1(S)-(tert.-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methyl-2′-(2(S)-methylbutyl)-2′-(p-toluenesulphonyl)valerohydrazide in the form of a gum. MS: 585 (M+H)+. Continued elution of the column gave 0.21 g of the hydrazide used in the reaction.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe ethyl acetate layer was washed with 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-6769c42d227f445e842471322a21724f
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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