Réaction #2843

ord-f4e8e6ec20fc45b7ba597aed2b56cab8

Équation de réaction

O=C([O-])[O-].[K+].[K+]
K2CO3
N#Cc1cccc(CN2CC[C@H](NS(=O)(=O)c3cc4ccccc4s3)C2=O)c1
benzo[b]thiophene-2-sulfonic acid [1-(3-cyano-benzyl)-2-oxo-pyrrolidin-3-(S)-yl]-amide
CI
methyl iodide
CN([C@H]1CCN(Cc2cccc(C#N)c2)C1=O)S(=O)(=O)c1cc2ccccc2s1
title compound
Rendement 96.7%
CN([C@H]1CCN(Cc2cccc(C#N)c2)C1=O)S(=O)(=O)c1cc2ccccc2s1
Benzo[b]thiophene-2-sulfonic acid [1-(3-cyanobenzyl)-2-oxo-pyrrolidin-3-(S)-yl]-methylamide
Rendement 96.7%

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    AutreThe layers are separated
  2. 2
    LavageThe organic layer is washed with H2O and saturated NaCl
  3. 3
    SéchageThe organic layer is dried over MgSO4
  4. 4
    Filtrationfiltered
  5. 5
    Concentrationconcentrated
  6. 6
    AutreThe residue is triturated with Et2O

Mode opératoire

To a solution of benzo[b]thiophene-2-sulfonic acid [1-(3-cyano-benzyl)-2-oxo-pyrrolidin-3-(S)-yl]-amide (0.25 g, 0.61 mmol) in 3 mL of DMF is added methyl iodide (0.13 g, 0.91 mmol) followed by K2CO3 (0.13 g, 0.91 mmol). The solution is stirred at ambient temperatures for 6 h. After this time, the solution is diluted with H2O and EtOAc. The layers are separated. The organic layer is washed with H2O and saturated NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The residue is triturated with Et2O to give the title compound (0.25 g, 0.59 mmol) as a white solid.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05731315uspto-grants-1998_03