p-Toluenesulfonic acid → Methyl 2-hydroxy-3-(2-(N-propyl-N-benzenesulfonylamino)ethoxy)-3,3-diphenylpropionate

HRID 1635081Notes

Reaction equation

HRID 1635081 reaction equation
[CH2:1]([N:4]([CH2:14][CH2:15][OH:16])[S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:7])=[O:6])[CH2:2][CH3:3].[O:17]1[C:23]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:18]1[C:19]([O:21][CH3:22])=[O:20].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[OH:17][CH:18]([C:23]([O:16][CH2:15][CH2:14][N:4]([CH2:1][CH2:2][CH3:3])[S:5]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)(=[O:7])=[O:6])([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:19]([O:21][CH3:22])=[O:20]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 10587027Methyl 3,3-diphenyloxirane-2-carboxylateHCID 18675618N-Propyl-N-(2-hydroxyethyl)benzenesulfonamide

Product 1

HCID 18675641Methyl 2-hydroxy-3-(2-(N-propyl-N-benzenesulfonylamino)ethoxy)-3,3-diphenylpropionate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

7.3 g (30 mmol) of N-propyl-N-(2-hydroxyethyl)benzenesulfonamide and 7.6 g (30 mmol) of methyl 2,3-epoxy-3,3-diphenylpropionate were dissolved in 40 ml of methylene chloride and, with ice-cooling, 0.57 g (3 mmol) of p-toluenesulfonic acid was added. The reaction mixture was stirred at room temperature for 24 hours and then diluted with methylene chloride and extracted with 2M aqueous sodium hydroxide solution, the organic phase was separated off and dried over sodium sulfate and the solvent was distilled off. The residue (12.0 g of an oil) was directly reacted further.

Workup

  1. temperaturecooling
  2. extractionextracted with 2M aqueous sodium hydroxide solution
  3. customthe organic phase was separated off
  4. dry with materialdried over sodium sulfate
  5. distillationthe solvent was distilled off
  6. customThe residue (12.0 g of an oil) was directly reacted further

Sources & evidence

ORD record
ord-6d094d9e34f94aa0bd41ec1c7dc14af6
Source dataset
uspto-grants-2003_01
Patent number
US06509341B1

Reaction notes

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