Triethylamine → 3-{2-[4-(3-Methoxy-propoxy)-3-methyl-pyridin-2-yl-methanesulfinyl]-benzimidazole-1-sulfonyl}-4-methylbenzoic acid 2-(toluene-4-sulfonyl)ethyl ester

HRID 2182876Notes

Reaction equation

HRID 2182876 reaction equation
[Na].[CH3:2][O:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([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])[C:9]=1[CH3:26].CCN(CC)CC.C([O-])(O)=O.[Na+].[C:39]1([CH3:64])[CH:44]=[CH:43][C:42]([S:45]([CH2:48][CH2:49][O:50][C:51](=[O:63])[C:52]2[CH:57]=[CH:56][C:55]([CH3:58])=[C:54]([S:59](Cl)(=[O:61])=[O:60])[CH:53]=2)(=[O:47])=[O:46])=[CH:41][CH:40]=1>C(Cl)Cl.O>[C:39]1([CH3:64])[CH:44]=[CH:43][C:42]([S:45]([CH2:48][CH2:49][O:50][C:51](=[O:63])[C:52]2[CH:57]=[CH:56][C:55]([CH3:58])=[C:54]([S:59]([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:10]3[C:9]([CH3:26])=[C:8]([O:7][CH2:6][CH2:5][CH2:4][O:3][CH3:2])[CH:13]=[CH:12][N:11]=3)=[O:16])(=[O:61])=[O:60])[CH:53]=2)(=[O:47])=[O:46])=[CH:41][CH:40]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 9821387(S)-Rabeprazole sodiumHCID 865925683-Chlorosulfonyl-4-methylbenzoic acid 2-(p-tolylsulfonyl)ethyl ester2×

Product 1

HCID 207864393-{2-[4-(3-Methoxy-propoxy)-3-methyl-pyridin-2-yl-methanesulfinyl]-benzimidazole-1-sulfonyl}-4-methylbenzoic acid 2-(toluene-4-sulfonyl)ethyl esterYield 82.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-[4-(3-methoxy-propoxy)-3-methyl-pyridin-2-yl-methanesulfinyl]-1H-benzimidazole sodium salt (RABEPRAZOLE sodium salt, 1.0 g, 2.62 mmol), 5 mL of Et3N, and about 1 g of NaHCO3 in CH2Cl2 (15 mL) was added the sulfonyl chloride (Intermediate 49, 1.30 g, 3.15 mmol, 1.2 eq) in CH2Cl2 (5 mL) at room temperature, and then the mixture was stirred for 0.5 h. Thereafter water was added, the mixture was extracted with CH2Cl2, and the organic layers were dried, and concentrated. The residual oil was purified by column chromatography (CH2Cl2 to 1% MeOH in CH2Cl2) to yield 1.6 g (80%) of 3-{2-[4-(3-methoxy-propoxy)-3-methyl-pyridin-2-yl-methanesulfinyl]-benzimidazole-1-sulfonyl}-4-methylbenzoic acid 2-(toluene-4-sulfonyl)ethyl ester (Intermediate 53) as an off-white foam.

Workup

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

Sources & evidence

ORD record
ord-8ddccf9cb48c43458b59745028b39cf2
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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