4-Toluenesulfonyl chloride → (2S,4R)-Methyl 1-benzoyl-4-(tosyloxy)pyrrolidine-2-carboxylate

HRID 1165961Notes

Reaction equation

HRID 1165961 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:12][O:13][C:14](=[O:29])[C@@H:15]1[CH2:19][C@@H:18]([OH:20])[CH2:17][N:16]1[C:21](=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.S(C1C=CC(C)=CC=1)([O-])(=O)=O>N1C=CC=CC=1>[CH3:12][O:13][C:14](=[O:29])[C@@H:15]1[CH2:19][C@@H:18]([O:20][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:17][N:16]1[C:21](=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 85570p-ToluenesulfonateHCID 1476249(2S,4R)-Methyl 1-benzoyl-4-hydroxypyrrolidine-2-carboxylate

Product 1

HCID 14750326(2S,4R)-Methyl 1-benzoyl-4-(tosyloxy)pyrrolidine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

540 Grams (2.84 moles) of technical p-toluenesulfonyl chloride were charged to a 5 liter flask. 1.5 Liters of anhydrous pyridine was added and the flask swirled to dissolve. Gradually, 600 g (2.40 moles) of (trans)-1-benzoyl-4-hydroxy-L-proline methyl ester were added and dissolved by swirling. The clear solution was maintained at room temperature and the conversion followed by TLC. After the starting material completely disappeared, the reaction mixture was transferred to a 12 liter beaker with an efficient agitator. 0.8 Liters of ice water and some tosylate seeds were added. Thick crystal slurry formed in about 10 minutes. Strong agitation was maintained and another 7 liters of an ice-water mixture were added over a period of one hour. The crystals were collected on a filter, the cake pressed down and washed with cold water until the effluent was free of chloride ions and suction applied to the cake until no more liquid emerged. The filtrate was discarded and the product dried to constant weight.

Workup

  1. dissolutionto dissolve
  2. dissolutiondissolved
  3. customThick crystal slurry formed in about 10 minutes
  4. temperatureStrong agitation was maintained
  5. customThe crystals were collected on a filter
  6. washwashed with cold water until the effluent
  7. customthe product dried to constant weight

Sources & evidence

ORD record
ord-7d3294b3e4f54dfbae30c6f1c3708629
Source dataset
uspto-grants-1990_03
Patent number
US04912231

Reaction notes

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