m-Xylyl bromide → 7-Methoxy-2-napthalenesulfonic acid [1-(3-cyanobenzyl)-2-oxopyrrolidin-3-(S)-yl](3-methylbenzyl)amide

HRID 619799Notes

Reaction equation

HRID 619799 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:29]=[CH:30][CH:31]=1)[CH2:6][N:7]1[CH2:11][CH2:10][C@H:9]([NH:12][S:13]([C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][C:20]([O:26][CH3:27])=[CH:21][CH:22]=3)[CH:17]=2)(=[O:15])=[O:14])[C:8]1=[O:28])#[N:2].[CH3:32][C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][CH:40]=1)[CH2:36]Br>>[C:1]([C:3]1[CH:4]=[C:5]([CH:29]=[CH:30][CH:31]=1)[CH2:6][N:7]1[CH2:11][CH2:10][C@H:9]([N:12]([CH2:32][C:33]2[CH:40]=[CH:39][CH:38]=[C:35]([CH3:36])[CH:34]=2)[S:13]([C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][C:20]([O:26][CH3:27])=[CH:21][CH:22]=3)[CH:17]=2)(=[O:15])=[O:14])[C:8]1=[O:28])#[N:2]

Participants

3

Reactant 2

HCID 12099m-Xylyl bromideHCID 105508547-methoxynaphtalene-2-sulfonic acid [1-(3-cyanobenzyl)-2-oxopyrrolidin-3-(S)-yl]amide

Product 1

HCID 673658487-Methoxy-2-napthalenesulfonic acid [1-(3-cyanobenzyl)-2-oxopyrrolidin-3-(S)-yl](3-methylbenzyl)amide

Procedure

The title compound is prepared as described in EXAMPLE 25, Part A using 7-methoxynaphthalene-2-sulfonic acid [1-(3-cyanobenzyl)-2-oxopyrrolidin-3-(S)-yl]amide, prepared as described in EXAMPLE 43, Part A, and 3-methylbenzyl bromide. The crude product is purified by column chromatography eluting with gradient of 40% EtOAc/hexanes to 50% EtOAc/hexanes to afford the title compound as a white foam.

Workup

  1. customThe title compound is prepared
  2. customprepared
  3. customThe crude product is purified by column chromatography
  4. washeluting with gradient of 40% EtOAc/hexanes to 50% EtOAc/hexanes

Sources & evidence

ORD record
ord-82ae8516bd3544c8b28157634a121253
Source dataset
uspto-grants-1999_09
Patent number
US05958918

Reaction notes

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