Triethylamine → HCID 20786424, compound

HRID 2182878Notes

Reaction equation

HRID 2182878 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:34]1([CH3:62])[CH:39]=[CH:38][C:37]([S:40]([CH2:43][CH2:44][O:45][C:46](=[O:61])[CH2:47][O:48][C:49]2[CH:54]=[C:53]([CH3:55])[C:52]([S:56](Cl)(=[O:58])=[O:57])=[C:51]([CH3:60])[CH:50]=2)(=[O:42])=[O:41])=[CH:36][CH:35]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:34]1([CH3:62])[CH:39]=[CH:38][C:37]([S:40]([CH2:43][CH2:44][O:45][C:46](=[O:61])[CH2:47][O:48][C:49]2[CH:50]=[C:51]([CH3:60])[C:52]([S:56]([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:57])=[O:58])=[C:53]([CH3:55])[CH:54]=2)(=[O:41])=[O:42])=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 9821387(S)-Rabeprazole sodiumHCID 86592569HCID 86592569, compound2×

Product 1

HCID 20786424HCID 20786424, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a heterogeneous 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) and 5 mL of Et3N in 20 mL of CH2Cl2 was added the chlorosulfonyl ester (Intermediate 13, 1.57 g, 3.41 mmol, 1.3 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 for 3 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 1.7 g (77%) of 3,5-dimethyl-4-{2-[4-(3-methoxy-propoxy)-3-methyl-pyridin-2-yl-methanesulfinyl]-benzimidazole-1-sulfonyl}phenoxyacetic acid 2-(toluene-4-sulfonyl)ethyl ester (Intermediate 58) as a 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-3d6814b9c952450aa5047e2245868f3e
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

Loading…