Anisole → HCID 15116364, compound

HRID 2166280Notes

Reaction equation

HRID 2166280 reaction equation
COC1C=CC(COC([N:11]2[CH2:15][C@@H:14]([S:16][C:17](=[O:19])[CH3:18])[CH2:13][C@H:12]2[C:20](=[O:29])[NH:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=O)=CC=1.C1(OC)C=CC=CC=1>FC(F)(F)C(O)=O>[CH2:22]([NH:21][C:20]([C@@H:12]1[CH2:13][C@H:14]([S:16][C:17](=[O:19])[CH3:18])[CH2:15][NH:11]1)=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 7519AnisoleHCID 15116363HCID 15116363, compound

Product 1

HCID 15116364HCID 15116364, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

177 mg of (2S,4S)-1-p-methoxybenzyloxycarbonyl-2-benzylcarbamoyl-4-acetylthiopyrrolidine and 86 mg of anisole were dissolved in 0.5 ml of trifluoroacetic acid, followed by stirring at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure, diluted with ethyl acetate, washed successively with an aqueous solution of sodium bicarbonate and water and dried over sodium sulfate. The solvent was removed by distillation, and the residue was subjected to silica gel thin layer chromatography to obtain (2S,4S)-2-benzylcarbamoyl-4-acetylthiopyrrolidine.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with ethyl acetate
  3. washwashed successively with an aqueous solution of sodium bicarbonate and water
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed by distillation

Sources & evidence

ORD record
ord-130123285afa4993bd3d6382bb7e231d
Source dataset
uspto-grants-1990_07
Patent number
US04943569

Reaction notes

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