Water → HCID 20786373, compound

HRID 2182861Notes

Reaction equation

HRID 2182861 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].[H-].[Na+].[N+:28]([C:31]1[CH:32]=[C:33]([S:37]([CH2:40][CH2:41][O:42][C:43](=[O:65])[CH2:44][CH2:45][CH2:46][NH:47][C:48](=[O:64])[CH2:49][O:50][C:51]2[CH:56]=[CH:55][C:54]([S:57](Cl)(=[O:59])=[O:58])=[C:53]([CH:61]([CH3:63])[CH3:62])[CH:52]=2)(=[O:39])=[O:38])[CH:34]=[CH:35][CH:36]=1)([O-:30])=[O:29].O>C(Cl)Cl>[N+:28]([C:31]1[CH:32]=[C:33]([S:37]([CH2:40][CH2:41][O:42][C:43](=[O:65])[CH2:44][CH2:45][CH2:46][NH:47][C:48](=[O:64])[CH2:49][O:50][C:51]2[CH:56]=[CH:55][C:54]([S:57]([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:59])=[O:58])=[C:53]([CH:61]([CH3:62])[CH3:63])[CH:52]=2)(=[O:38])=[O:39])[CH:34]=[CH:35][CH:36]=1)([O-:30])=[O:29]

Participants

6

Reactant 4

HCID 962WaterHCID 3883LansoprazoleHCID 24758Sodium hydrideHCID 131724895HCID 131724895, compound2×

Product 1

HCID 20786373HCID 20786373, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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) was added NaH (40 mg, 1.65 mmol) at room temperature resulting in a clear solution. To this clear mixture was added 4-(4-chlorosulfonyl-3-Isopropylphenoxyactamido)-butyric acid 2-(3-nitrobenzenesulfonyl)ethyl ester (Intermediate 26, 1.0 g, 1.70 mmol, 1.25 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, 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 Intermediate 27 (1.0 g, 80%) as an off-white foam.

Workup

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

Sources & evidence

ORD record
ord-c0a6154332c34d42b484c7e05d40dee7
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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