Potassium Carbonate → 7-Methoxy-2-napthalenesulfonic acid [1-(3-cyanobenzyl)-2-oxopyrrolidin-3-(S)-yl]-(2-methoxybenzyl)amide

HRID 619809Notes

Reaction equation

HRID 619809 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].C([O-])([O-])=O.[K+].[K+].[CH3:38][O:39][C:40]1[CH:47]=[CH:46][CH:45]=[CH:44][C:41]=1[CH2:42]Cl>CC(C)=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[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]([CH2:42][C:41]2[CH:44]=[CH:45][CH:46]=[CH:47][C:40]=2[O:39][CH3:38])[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

7

Reactant 3

HCID 11430Potassium CarbonateHCID 814952-(Chloromethyl)anisoleHCID 105508547-methoxynaphtalene-2-sulfonic acid [1-(3-cyanobenzyl)-2-oxopyrrolidin-3-(S)-yl]amide

Product 1

HCID 673658677-Methoxy-2-napthalenesulfonic acid [1-(3-cyanobenzyl)-2-oxopyrrolidin-3-(S)-yl]-(2-methoxybenzyl)amide

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-methoxynaphtalene-2-sulfonic acid [1-(3-cyanobenzyl)-2-oxopyrrolidin-3-(S)-yl]amide (0.12 g, 0.26 mmol), prepared as described in EXAMPLE 43, part A, in 20 mL of acetone is added K2CO3 (0.07 g, 0.53 mmol), 2-methoxybenzyl chloride (0.09 g, 0.28 mmol) and tetrabutylammonium iodide (0.02 g, 0.05 mmol). The resulting mixture is stirred for 48 hours, then diluted with CH2Cl2 and washed with saturated NaHCO3, H2O and saturated NaCl. The organic layer is dried over MgSO4, filtered, and concentrated. The crude product is purified by column chromatography eluting with 3% MeOH/CH2Cl2 to afford the title compound as a white foam.

Workup

  1. washwashed with saturated NaHCO3, H2O and saturated NaCl
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product is purified by column chromatography
  6. washeluting with 3% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-1343ab5d2cf04808bd99b320132fba4d
Source dataset
uspto-grants-1999_09
Patent number
US05958918

Reaction notes

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