Lansoprazole → Dexlansoprazole

HRID 16931

Reaction equation

HRID 16931 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].CCCCCC.CC(O)C.C(O)C>C(#N)C>[CH3:1][C:2]1[C:3]([CH2:14][S@:15]([C:17]2[NH:18][C:19]3[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=3[N:21]=2)=[O:16])=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:13])([F:11])[F:12]

Participants

4

Reactant 2

HCID 3883LansoprazoleHCID 22572948Hexane 2-propanol ethanol

Product 1

HCID 9578005DexlansoprazoleYield 40.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazole (lansoprazole) (racemate) (3.98 g) was dissolved in the following mobile phase (330 ml) and acetonitrile (37 ml) and fractionated by HPLC (column: CHIRALCEL OD 20 mm dia.×250 mm, temperature: 30° C., mobile phase: hexane/2-propanol/ethanol=255/35/10, flowrate: 16 ml/min, detection wavelength: 285 nm, 1 shot: 20-25 mg). Fractions of optical isomers of shorter retention time were combined and concentrated; the individual lots were combined and dissolved in ethanol and filtered through a 0.45 μm filter; after hexane was added, the filtrate was again evaporated to dryness to yield R(+)-lansoprazole (1.6 g, optical purity >97.6% ee) as an amorphous substance.

Workup

  1. concentrationconcentrated
  2. dissolutiondissolved in ethanol
  3. filtrationfiltered through a 0.45 μm
  4. filtrationfilter
  5. additionafter hexane was added
  6. customthe filtrate was again evaporated to dryness

Sources & evidence

ORD record
ord-52015cb62b724e32ad271bcd9e6e1bd5
Source dataset
uspto-grants-2010_06
Patent number
US07737282B2

Linked notes

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