Lansoprazole → 3-[2-Methoxy-5-{2-(3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl-methanesulfinyl)-benzimidazole-1-sulfonyl}phenyl]propionic Acid 2-(toluene-4-sulfonyl)ethyl Ester

HRID 2182882Notes

Reaction equation

HRID 2182882 reaction equation
[CH3:1][C:2]1[C:3]([CH2:14][S:15]([C:17]2[NH:21][C:20]3[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=3[N:18]=2)=[O:16])=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11].CCN(CC)CC.[C:33]1([CH3:61])[CH:38]=[CH:37][C:36]([S:39]([CH2:42][CH2:43][O:44][C:45](=[O:60])[CH2:46][CH2:47][C:48]2[CH:53]=[C:52]([S:54](Cl)(=[O:56])=[O:55])[CH:51]=[CH:50][C:49]=2[O:58][CH3:59])(=[O:41])=[O:40])=[CH:35][CH:34]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:33]1([CH3:61])[CH:38]=[CH:37][C:36]([S:39]([CH2:42][CH2:43][O:44][C:45](=[O:60])[CH2:46][CH2:47][C:48]2[CH:53]=[C:52]([S:54]([N:21]3[C:20]4[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=4[N:18]=[C:17]3[S:15]([CH2:14][C:3]3[C:2]([CH3:1])=[C:7]([O:8][CH2:9][C:10]([F:13])([F:11])[F:12])[CH:6]=[CH:5][N:4]=3)=[O:16])(=[O:56])=[O:55])[CH:51]=[CH:50][C:49]=2[O:58][CH3:59])(=[O:41])=[O:40])=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 3883LansoprazoleHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 865925703-(5-Chlorosulfonyl-2-methoxyphenyl)propionic acid 2-(toluene-4-sulfonyl)ethyl ester2×

Product 1

HCID 207864413-[2-Methoxy-5-{2-(3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl-methanesulfinyl)-benzimidazole-1-sulfonyl}phenyl]propionic Acid 2-(toluene-4-sulfonyl)ethyl EsterYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a heterogeneous solution of 2-[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl-methanesulfinyl]-1H-benzimidazole (LANSOPRAZOLE, 800 mg, 2.17 mmol) and 3 mL of Et3N in 20 mL of CH2Cl2 was added the chlorosulfonyl ester (Intermediate 60, 1.2 g, 2.60 mmol, 1.2 eq). About 1 g of solid NaHCO3 was added after the chlorosulfonyl ester has dissolved completely in the reaction mixture. The mixture was stirred at room temperature 1 h. Thereafter the solvent was removed by evaporation and the residual oil was purified by column chromatography (silica gel, CH2Cl2 to 1% MeOH in CH2Cl2) to give Intermediate 63 (1.2 g, 70%) as an off-white foam.

Workup

  1. dissolutionhas dissolved completely in the reaction mixture
  2. customThereafter the solvent was removed by evaporation
  3. customthe residual oil was purified by column chromatography (silica gel, CH2Cl2 to 1% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-4424bae3e8c0462e93e855bed288a4a3
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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