Benzyl bromoacetate → Diethylether hexane

HRID 2229354Notes

Reaction equation

HRID 2229354 reaction equation
[Na].Br[CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=O>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:12][CH2:13][CH2:8][CH2:9][CH2:10][CH3:11].[CH3:3][CH2:4][O:6][CH2:7][CH3:8]

Participants

5

Reactant 2

HCID 62576Benzyl bromoacetateHCID 5360545Sodium

Product 1

HCID 21584099Diethylether hexaneYield 141%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

Sodium salt H-1a (1.13 g; 3.15 mmol) was suspended in 5 mL dry toluene and tetra-n-butyl ammonium bromide (0.10 g; 0.3 mmol) and benzyl bromoacetate (0.79 g; 3.45 mmol) were added and the solution was refluxed for 24 h. The solvent was removed and methylene chloride added to the residue. The solution was filtered through silica gel, the filtrate was evaporated and the crude product E-1k purified by flash chromatography using silica gel and a hexane/ether gradient (0.39 g; 26% yield). 1H NMR (CDCl3): δ0.95 (dd,6H), 1.45 (s,9H), 1.78 (m,2H), 1.92 (m,1H), 3.28-3.55 (m,4H), 4.08 (t,1H), 4.32 (s,2H), 5.07 (br t, 1H), 5.21 (s,2H), 7.34 (m,5H). 13C NMR: δ22.36, 24.34, 28.26, 39.03, 39.64, 40.42, 47.87, 64.77, 67.89, 79.71, 128.28, 128.37, 128.57, 134.59, 155.78, 165.38, 166.84. This derivative of E-1, E-1k, can be readily deblocked and elaborated further to yield additional inhibitors.

Workup

  1. temperaturethe solution was refluxed for 24 h
  2. customThe solvent was removed
  3. additionmethylene chloride added to the residue
  4. filtrationThe solution was filtered through silica gel
  5. customthe filtrate was evaporated
  6. customthe crude product E-1k purified by flash chromatography

Sources & evidence

ORD record
ord-ea26c087a8ab405784a1eda95cc04d48
Source dataset
uspto-grants-2002_07
Patent number
US06420401B1

Reaction notes

Loading…