Reaction #738794

ord-365acb1593ca45f7bdeac6a629f95c85

Reaction equation

O=S(=O)(Cl)c1cc2ccccc2s1
benzo[b]thiophene-2-sulfonyl chloride
Cl.N[C@H]1CCN(Cc2ccc3ccc(Cl)nc3c2)C1=O
7-(3-(S)-amino-2-oxopyrrolidin-1-ylmethyl)-2-chloro-quinoline hydrochloride
COc1ccc2ccc(S(=O)(=O)Cl)cc2c1
7-methoxynaphthalene-2-sulfonyl chloride
→
O=C1[C@@H](NS(=O)(=O)c2cc3ccccc3s2)CCN1Cc1ccc2ccc(Cl)nc2c1
title compound
O=C1[C@@H](NS(=O)(=O)c2cc3ccccc3s2)CCN1Cc1ccc2ccc(Cl)nc2c1
Benzo[b]thiophene-2-sulfonic acid [1-(2-chloro-quinolin-7-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]-amide

Reactants

O=S(=O)(Cl)c1cc2ccccc2s1
benzo[b]thiophene-2-sulfonyl chloride
Cl.N[C@H]1CCN(Cc2ccc3ccc(Cl)nc3c2)C1=O
7-(3-(S)-amino-2-oxopyrrolidin-1-ylmethyl)-2-chloro-quinoline hydrochloride
COc1ccc2ccc(S(=O)(=O)Cl)cc2c1
7-methoxynaphthalene-2-sulfonyl chloride

Reagents

None

Solvents

ClC(Cl)Cl
CHCl3

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe crude product is triturated from CH2Cl2

Procedure

The title compound is prepared in CHCl3 instead of CH3CN from 7-(3-(S)-amino-2-oxopyrrolidin-1-ylmethyl)-2-chloro-quinoline hydrochloride as described in EXAMPLE 1, Part K using benzo[b]thiophene-2-sulfonyl chloride as prepared in EXAMPLE 8, Part A in place of 7-methoxynaphthalene-2-sulfonyl chloride. The crude product is triturated from CH2Cl2 to afford the title compound as a beige solid.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06281227B1uspto-grants-2001_08