p-Toluenesulfonic acid → HCID 18675620, compound

HRID 1635082Notes

Reaction equation

HRID 1635082 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[O:15]1[C:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:16]1[C:17]([O:19][CH3:20])=[O:18].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[OH:15][CH:16]([C:21]([O:1][CH2:2][CH2:3][NH:4][C:5]([O:6][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:14])([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:17]([O:19][CH3:20])=[O:18]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 280458benzyl N-(2-hydroxyethyl)carbamateHCID 10587027Methyl 3,3-diphenyloxirane-2-carboxylate

Product 1

HCID 18675620HCID 18675620, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

9.8 g (50 mmol) of benzyl (2-hydroxyethyl)carbamate and 12.7 g (50 mmol) of methyl 2,3-epoxy-3,3-diphenylpropionate were dissolved in 80 ml of methylene chloride and, with ice-cooling, 0.95 g (5 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 (22.2 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 (22.2 g of an oil) was directly reacted further

Sources & evidence

ORD record
ord-a125b0b1550b4cf8b0727e5c35acea60
Source dataset
uspto-grants-2003_01
Patent number
US06509341B1

Reaction notes

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