Tetrabutylammonium Hydroxide → Tetrabutylammonium benzyl adipate

HRID 1461997Notes

Reaction equation

HRID 1461997 reaction equation
[C:1]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O-:8])=[O:7].[OH-].[CH2:19]([N+:23]([CH2:32][CH2:33][CH2:34][CH3:35])([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:21][CH3:22]>C(Cl)(Cl)Cl.O>[CH2:11]([O:10][C:1](=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O-:8])=[O:7])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH2:32]([N+:23]([CH2:19][CH2:20][CH2:21][CH3:22])([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:28][CH2:29][CH2:30][CH3:31])[CH2:33][CH2:34][CH3:35]

Participants

5

Reactant 2

HCID 2723671Tetrabutylammonium HydroxideHCID 19019622Benzyl adipate

Product 1

HCID 14479936Tetrabutylammonium benzyl adipate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To 11.8 g (0.05 mole) benzyl adipate half ester in 250 ml chloroform and 40 ml water is added 40% aqueous tetrabutylammonium hydroxide with vigorous stirring until the mixture is pH 8.5. The organic phase is separated, the aqueous layer extracted with chloroform and the combined extracts dried over anhydrous sodium sulfate. Evaporation of solvent gives tetrabutylammonium benzyl adipate as an oil. The oil is mixed with toluene (250 ml) and 2.56 g (0.05 mole) iodomethyl 6-[D-(2-azido-2-phenylacetamido)]-penicillanate is added. The mixture is stirred for one hour, diluted to 500 ml with ethyl acetate and the precipitated tetrabutylammonium iodide removed by filtration, washing with ethyl acetate. The filtrate and washings are washed with sodium bicarbonate solution, water, brine and dried (Na2SO4). Evaporation of solvent affords the title compound which is purified by silica gel chromatography.

Workup

  1. customThe organic phase is separated
  2. extractionthe aqueous layer extracted with chloroform
  3. dry with materialthe combined extracts dried over anhydrous sodium sulfate
  4. customEvaporation of solvent

Sources & evidence

ORD record
ord-65fd8129ec014255aef99cc356193869
Source dataset
uspto-grants-1984_07
Patent number
US04457924

Reaction notes

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