Lansoprazole → HCID 20786423, compound

HRID 2182843

Reaction equation

HRID 2182843 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+].C1(C)C=CC(S(CCOC(=O)C)(=O)=O)=CC=1.[C:44]1([CH3:70])[CH:49]=[CH:48][C:47]([S:50]([CH2:53][CH2:54][O:55][C:56](=[O:69])[CH2:57][O:58][C:59]2[CH:64]=[CH:63][C:62]([S:65](Cl)(=[O:67])=[O:66])=[CH:61][CH:60]=2)(=[O:52])=[O:51])=[CH:46][CH:45]=1.C([O-])(O)=O.[Na+].ClS([O-])(=O)=O>C(Cl)Cl>[C:44]1([CH3:70])[CH:49]=[CH:48][C:47]([S:50]([CH2:53][CH2:54][O:55][C:56](=[O:69])[CH2:57][O:58][C:59]2[CH:64]=[CH:63][C:62]([S:65]([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:66])=[O:67])=[CH:61][CH:60]=2)(=[O:52])=[O:51])=[CH:46][CH:45]=1

Participants

8

Reactant 6

HCID 3883LansoprazoleHCID 24758Sodium hydrideHCID 516892Sodium Bicarbonate2×HCID 21989438SulfurochloridateHCID 58426230HCID 58426230, compoundHCID 59316688HCID 59316688, compound

Product 1

HCID 20786423HCID 20786423, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a heterogeneous solution of 2-[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-ylmethanesulfinyl]-1H-benzimidazole (900 mg, 2.44 mmol) in 30 mL of CH2Cl2 was added 70 mg of NaH (2.92 mmol) at room temperature, during which time the mixture became homogeneous. To this clear reaction mixture was added the 4-chlorosulfonylphenoxy)acetic acid 2-(toluene-4-sulfonyl)ethyl ester (Intermediate 4, 1.26 g, 2.92 mmol, 1.2 eq). About 1 g of solid NaHCO3 was added after the chlorosulfonate has dissolved completely in the reaction mixture. (Without addition of NaHCO3 the mixture became black when the reaction was complete.) Thereafter the solvent was removed by evaporation and the residual oil was purified by column chromatography (silica gel, CH2Cl2 to 4% MeOH in CH2Cl2) to give 1.75 g (94%) of the desired product (Intermediate 5) as an off-white foam.

Workup

  1. dissolutionhas dissolved completely in the reaction mixture
  2. custom) Thereafter the solvent was removed by evaporation
  3. customthe residual oil was purified by column chromatography (silica gel, CH2Cl2 to 4% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-fedb963048944885a00ed1ff4b580582
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Linked notes

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