Benzyl Bromide → (E)-benzyl-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvalerate

HRID 1979261Notes

Reaction equation

HRID 1979261 reaction equation
[C:1]([O:5][C:6]([C@H:8]([C@@H:18]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:19]([OH:21])=[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+].[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CN(C)C=O>[CH2:32]([O:20][C:19](=[O:21])[C@@H:18]([C@@H:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]/[CH:10]=[CH:11]/[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH2:22][CH:23]([CH3:25])[CH3:24])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 11418712(E)-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvaleric acid

Product 1

HCID 69953806(E)-benzyl-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvalerate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.0 g of (E)-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvaleric acid in 10 ml of dimethylformamide was treated in succession with 2.0 g of potassium carbonate and 0.45 ml of benzyl bromide. The mixture was stirred at room temperature for 1 hour and then the solvent was evaporated and the residue was dissolved in ethyl acetate and washed with water until the water washings were neutral (pH=7). Drying over anhydrous magnesium sulfate and evaporation gave 1.28 g of (E)-benzyl-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvalerate in the form of an orange oil.

Workup

  1. customthe solvent was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water until the water washings
  4. dry with materialDrying over anhydrous magnesium sulfate and evaporation

Sources & evidence

ORD record
ord-95d2c052471048a88edb282bea41ed99
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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