Water → 6-[2-(4-{2-[3-Methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}-phenoxy)acetylamino]hexanoic acid 2-(3-nitrobenzenesulfonyl)ethyl ester

HRID 2182856Notes

Reaction equation

HRID 2182856 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([CH2:13][CH2:14][O:15][C:16](=[O:37])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:36])[CH2:24][O:25][C:26]2[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH3:38][C:39]1[C:40]([CH2:51][S:52]([C:54]2[NH:58][C:57]3[CH:59]=[CH:60][CH:61]=[CH:62][C:56]=3[N:55]=2)=[O:53])=[N:41][CH:42]=[CH:43][C:44]=1[O:45][CH2:46][C:47]([F:50])([F:49])[F:48].[H-].[Na+].O>C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([CH2:13][CH2:14][O:15][C:16](=[O:37])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:36])[CH2:24][O:25][C:26]2[CH:31]=[CH:30][C:29]([S:32]([N:55]3[C:56]4[CH:62]=[CH:61][CH:60]=[CH:59][C:57]=4[N:58]=[C:54]3[S:52]([CH2:51][C:40]3[C:39]([CH3:38])=[C:44]([O:45][CH2:46][C:47]([F:48])([F:49])[F:50])[CH:43]=[CH:42][N:41]=3)=[O:53])(=[O:34])=[O:33])=[CH:28][CH:27]=2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 3883LansoprazoleHCID 24758Sodium hydrideHCID 865925656-[2-(4-Chlorosulfonyl-phenoxy)-acetylamino]-n-hexanoic acid 2-(3-nitro-benzenesulfonyl)ethyl ester2×

Product 1

HCID 207863756-[2-(4-{2-[3-Methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}-phenoxy)acetylamino]hexanoic acid 2-(3-nitrobenzenesulfonyl)ethyl esterYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

6-[2-(4-chlorosulfonyl-phenoxy)-acetylamino]-n-hexanoic acid 2-(3-nitro-benzenesulfonyl)ethyl ester (Intermediate 19, 1.0 g, 1.73 mmol, 1.27 eq) in CH2Cl2 (5 mL) was added to a heterogeneous mixture of 2-[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-ylmethanesulfinyl]-1H-benzimidazole (500 mg, 1.36 mmol) in CH2Cl2 (10 mL) and NaH (40 mg, 1.65 mmol) at room temperature, and 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 under reduced pressure. The residual oil was purified by column chromatography (CH2Cl2 to 3% MeOH in CH2Cl2) to yield 6-[2-(4-{2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}-phenoxy)acetylamino]hexanoic acid 2-(3-nitrobenzenesulfonyl)ethyl ester (Intermediate 20, 1.15 g, 94%) as an off-white foam.

Workup

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

Sources & evidence

ORD record
ord-74b5b4c58a744b1cb858c42eca8babdc
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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