Water → Dexlansoprazole

HRID 1609881Notes

Reaction equation

HRID 1609881 reaction equation
[CH3:1][C:2]1[C:3]([CH2:14][S:15][C:16]2[NH:17][C:18]3[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=3[N:20]=2)=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11].O.C(C(C(C(OCC)=O)O)O)(OCC)=[O:27].C(N(C(C)C)CC)(C)C.[O-]O.C1(C(C)C)C=CC=CC=1>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].C1(C)C=CC=CC=1>[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)=[O:27])=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:12])([F:11])[F:13]

Participants

8

Reactant 5

HCID 962WaterHCID 62333Butanedioic acid, 2,3-dihydroxy-, diethyl ester, S-(R*,R*)-HCID 81531DiisopropylethylamineHCID 1094080Lansoprazole sulfideHCID 53627471Cumen hydroperoxide

Product 1

HCID 9578005Dexlansoprazole

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
55 °C

Procedure

2-[[[3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]thio]benzimidazole (50.0 g, 0.14 mol), toluene (244 ml), water (233 mg, 0.013 mol, total water content 0.013 mol) and diethyl (+)-tartrate (10.6 ml, 0.062 mol) were mixed, and titanium(IV) isopropoxide (8.3 ml, 0.025 mol) was added at 50 to 60° C. The mixture was stirred at 50 to 60° C. for 30 min. Diisopropylethylamine (8.14 ml, 0.047 mol) was added to the obtained mixture at room temperature and then cumene hydroperoxide (76.4 ml, content 82%, 0.43 mol) was added at −5 to 5° C. The mixture was reacted by stirring at −5 to 5° C. for 1.5 hr.

Workup

  1. customThe mixture was reacted
  2. stirringby stirring at −5 to 5° C. for 1.5 hr

Sources & evidence

ORD record
ord-3db23bbbeb214c0ca90e282ca58b211e
Source dataset
uspto-grants-2006_01
Patent number
US06982275B2

Reaction notes

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