m-Chloroperbenzoic acid → Lansoprazole

HRID 2230242Notes

Reaction equation

HRID 2230242 reaction equation
[CH3:1][C:2]1[C:3]([CH2:14][S:15][C:16]2[NH:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[N:17]=2)=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11].ClC1C=CC=C(C(OO)=[O:33])C=1>C(Cl)(Cl)Cl>[CH3:1][C:2]1[C:7]([O:8][CH2:9][C:10]([F:12])([F:11])[F:13])=[CH:6][CH:5]=[N:4][C:3]=1[CH2:14][S+:15]([O-:33])[C:16]1[NH:20][C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[N:17]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 1094080Lansoprazole sulfide

Product 1

HCID 3883LansoprazoleYield 60%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2.23 g of 2-[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methylthio-1H-benzimidazole(6 mmol) prepared in Example 1 was dissolved in 20 ml of chloroform, 1.24 g of m-chloroperbenzoic acid(1.2 equivalent) dissolved in 20 ml of chloroformwas added thereto dropwise at below 5° C., and stirred at the same temperature for about 10 minutes. The reaction mixture was washed with aqueous NaHCO3 and dried over MgSO4. The residue obtained after removing the solvent under a reduced pressure was purified by silica gel column chromatography and recrystallization, to obtain 1.33 g of lansoprazole as a white-light brown solid (yield: 60%).

Workup

  1. additionadded
  2. washThe reaction mixture was washed with aqueous NaHCO3
  3. dry with materialdried over MgSO4
  4. customThe residue obtained
  5. customafter removing the solvent under a reduced pressure
  6. customwas purified by silica gel column chromatography and recrystallization

Sources & evidence

ORD record
ord-741e0e431434438eae118fb849a55459
Source dataset
uspto-grants-2002_07
Patent number
US06423846B1

Reaction notes

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