Lansoprazole → 3-{2-[3-Methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-yl-methanesulfinyl]-benzimidazole-1-sulfonyl}-4-methylbenzoic acid 2-(toluene-4-sulfonyl)ethyl ester

HRID 2182875Notes

Reaction equation

HRID 2182875 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([O-])(O)=O.[Na+].[C:38]1([CH3:63])[CH:43]=[CH:42][C:41]([S:44]([CH2:47][CH2:48][O:49][C:50](=[O:62])[C:51]2[CH:56]=[CH:55][C:54]([CH3:57])=[C:53]([S:58](Cl)(=[O:60])=[O:59])[CH:52]=2)(=[O:46])=[O:45])=[CH:40][CH:39]=1>C(Cl)Cl.O>[C:38]1([CH3:63])[CH:43]=[CH:42][C:41]([S:44]([CH2:47][CH2:48][O:49][C:50](=[O:62])[C:51]2[CH:56]=[CH:55][C:54]([CH3:57])=[C:53]([S:58]([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:60])=[O:59])[CH:52]=2)(=[O:46])=[O:45])=[CH:40][CH:39]=1

Participants

7

Reactant 4

HCID 3883LansoprazoleHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 865925683-Chlorosulfonyl-4-methylbenzoic acid 2-(p-tolylsulfonyl)ethyl ester2×

Product 1

HCID 207864613-{2-[3-Methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-yl-methanesulfinyl]-benzimidazole-1-sulfonyl}-4-methylbenzoic acid 2-(toluene-4-sulfonyl)ethyl esterYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a heterogeneous mixture of 2-[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl-methanesulfinyl]-1H-benzimidazole (LANSOPRAZOLE, 700 mg, 1.89 mmol), 3 mL of Et3N, and about 1 g of NaHCO3 in CH2Cl2 (15 mL) was added the sulfonyl chloride (Intermediate 49, 1.03 g, 2.47 mmol, 1.3 eq) in CH2Cl2 (5 mL) at room temperature, and then the mixture was stirred for 2 h. Thereafter water was added, the mixture was extracted with CH2Cl2, and the organic layers were dried, and concentrated. The resulting residual oil was purified by column chromatography (CH2Cl2 to 1% MeOH in CH2Cl2) to yield 1.1 g (78%) of 3-{2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-yl-methanesulfinyl]-benzimidazole-1-sulfonyl}-4-methylbenzoic acid 2-(toluene-4-sulfonyl)ethyl ester (Intermediate 52) as a yellow foam.

Workup

  1. extractionthe mixture was extracted with CH2Cl2
  2. customthe organic layers were dried
  3. concentrationconcentrated
  4. customThe resulting residual oil was purified by column chromatography (CH2Cl2 to 1% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-0ced629873974f57abe8f3c87ee1de7f
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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