p-Toluenesulfonic acid → methyl 2-hydroxy-3-(N,N-dibutylcarbamoylmethoxy)-3,3-diphenylpropionate

HRID 1635078Notes

Reaction equation

HRID 1635078 reaction equation
[CH2:1]([N:5]([CH2:10][CH2:11][CH2:12][CH3:13])[C:6](=[O:9])[CH2:7][OH:8])[CH2:2][CH2:3][CH3:4].[O:14]1[C:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:15]1[C:16]([O:18][CH3:19])=[O:17].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[OH:14][CH:15]([C:20]([O:8][CH2:7][C:6](=[O:9])[N:5]([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:1][CH2:2][CH2:3][CH3:4])([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:16]([O:18][CH3:19])=[O:17]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 10587027Methyl 3,3-diphenyloxirane-2-carboxylateHCID 11008655N,N-Dibutyl-2-hydroxyacetamide

Product 1

HCID 18675624methyl 2-hydroxy-3-(N,N-dibutylcarbamoylmethoxy)-3,3-diphenylpropionateYield 45.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.3 g of N,N-di-n-butyl-2-hydroxyacetamide and 1.8 g of methyl 2,3-epoxy-3,3-diphenylpropionate were dissolved in 30 ml of methylene chloride and, while cooling in ice, a catalytic amount of p-toluenesulfonic acid was added. The mixture was stirred at room temperature for 24 hours and then added to sodium bicarbonate solution, the organic phase was separated off and dried over magnesium sulfate, and the solvent was distilled off. The residue was purified by chromatography, and 1.4 g of an oil were isolated and were immediately reacted further.

Workup

  1. temperaturewhile cooling in ice
  2. customthe organic phase was separated off
  3. dry with materialdried over magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-e2e290b282f44aa7a353a227f68aaac6
Source dataset
uspto-grants-2003_01
Patent number
US06509341B1

Reaction notes

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