Water → Lansoprazole

HRID 1665821Notes

Reaction equation

HRID 1665821 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].C(O[O-])(=O)C1C(=CC=CC=1)C([O-])=[O:29].[Mg+2].O>C(O)C>[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-:29])[C:16]1[NH:20][C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[N:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1094080Lansoprazole sulfideHCID 10130449Monoperoxyphthalic Acid Magnesium Salt

Product 1

HCID 3883LansoprazoleYield 165.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.0 g (2.8 mmol) of 2-([3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]-methyl)thio-1H-benzimidazole was dissolved in 20 Ml of 95% ethanol, and cooled to −20˜−10° C. 1.0 g (1.6 mmol) of 80% MMPP (magnesium monoperoxyphthalate) was added thereto, and the resulting mixture was stirred for 4 hours at the same temperature. Completion of the reaction was confirmed by TLC and HPLC, and 10 Ml of water was added to the reaction mixture, which was then stirred for 1 hour under ice-cooling. The reaction mixture was filtered to separate crystal, and thus separated crystal was washed with ice-cooled isopropanol-water mixture (1:1), and dried under reduced pressure, to give 0.98 g (Yield 95%) of Lansoprazole as white solid.

Workup

  1. temperaturecooled to −20˜−10° C
  2. additionwas added to the reaction mixture, which
  3. stirringwas then stirred for 1 hour under ice-
  4. temperaturecooling
  5. filtrationThe reaction mixture was filtered
  6. customto separate crystal, and thus separated crystal
  7. washwas washed with ice-
  8. temperaturecooled isopropanol-water mixture (1:1)
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-9018241a73ac4e1c8514f07147f55f69
Source dataset
uspto-grants-2011_10
Patent number
US08039631B2

Reaction notes

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