p-Toluenesulfonic acid → (2S,4R)-2-(2-formylthiazol-4-yl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 37272Notes

Reaction equation

HRID 37272 reaction equation
C[O:2][CH:3](OC)[C:4]1[S:5][CH:6]=[C:7]([C@@H:9]2[CH2:13][C@@H:12]([O:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH2:11][N:10]2[C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)=[O:20])[N:8]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[CH:3]([C:4]1[S:5][CH:6]=[C:7]([C@@H:9]2[CH2:13][C@@H:12]([O:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH2:11][N:10]2[C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)=[O:20])[N:8]=1)=[O:2]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 15077761(2S,4R)-2-[2-(dimethoxymethyl)thiazol-4-yl]-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Product 1

HCID 15077762(2S,4R)-2-(2-formylthiazol-4-yl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidineYield 95.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of (2S, 4R)-2-[2-(dimethoxymethyl)-thiazol-4-yl]-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl) pyrrolidine (2.6 g) in acetone (100 ml) was added p-toluenesulfonic acid (0.49 g) at room temperature. After stirring under reflux for 1 hour, the mixture was evaporated. The residue was dissolved in ethyl acetate, washed in turn with saturated aqueous sodium bicarbonate and brine, and dried over magnesium sulfate. The organic layer was evaporated to give (2S,4R)-2-(2-formylthiazol-4-yl) -4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl) pyrrolidine (2.26 g).

Workup

  1. temperatureunder reflux for 1 hour
  2. customthe mixture was evaporated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed in turn with saturated aqueous sodium bicarbonate and brine
  5. dry with materialdried over magnesium sulfate
  6. customThe organic layer was evaporated

Sources & evidence

ORD record
ord-621b966d77d84bd5b990a0ba6fda059e
Source dataset
uspto-grants-1995_05
Patent number
US05420122

Reaction notes

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