4-Toluenesulfonyl chloride → (cis)-1-Benzoyl-4-tosyloxy-L-proline, methyl ester

HRID 1165970Notes

Reaction equation

HRID 1165970 reaction equation
[C:1]([N:9]1[CH2:17][C@@H:16]([OH:18])[CH2:15][C@H:10]1[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.C(OCC)(=O)C>N1C=CC=CC=1>[C:1]([N:9]1[CH2:17][C@@H:16]([O:18][S:25]([C:22]2[CH:23]=[CH:24][C:19]([CH3:29])=[CH:20][CH:21]=2)(=[O:27])=[O:26])[CH2:15][C@H:10]1[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chloride2×HCID 8857Ethyl AcetateHCID 1476251(2S,4S)-Methyl 1-benzoyl-4-hydroxypyrrolidine-2-carboxylate

Product 1

HCID 14750327(cis)-1-Benzoyl-4-tosyloxy-L-proline, methyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (cis)-1-benzoyl-4-hydroxy-L-proline, methyl ester (1.9 g, 7.63 mmole) in pyridine (6 ml) was stirred under argon and treated with p-toluenesulfonyl chloride (1.75 g, 9.16 mmole). The reaction was stirred overnight, treated with additional p-toluenesulfonyl chloride (0.145 g, 0.76 mmole) and stirred for 24 hours. Ice water was added followed by ethyl acetate. The organic layer was washed with 1N HCl, brine, and dried. Filtration and concentration in vacuo afforded the title compound as a foam which was used without purification in the subsequent step.

Workup

  1. stirringstirred for 24 hours
  2. washThe organic layer was washed with 1N HCl, brine
  3. customdried
  4. filtrationFiltration and concentration in vacuo

Sources & evidence

ORD record
ord-3ac2b969e75647518d0e328c0e425599
Source dataset
uspto-grants-1990_03
Patent number
US04912231

Reaction notes

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