Water → Lansoprazole
Reaction equation
O.C([C@@H]([C@H](C(OCC)=O)O)O)(OCC)=[O:3].[CH3:16][C:17]1[C:18]([CH2:29][S:30][C:31]2[NH:35][C:34]3[CH:36]=[CH:37][CH:38]=[CH:39][C:33]=3[N:32]=2)=[N:19][CH:20]=[CH:21][C:22]=1[O:23][CH2:24][C:25]([F:28])([F:27])[F:26].C(N(CC)C(C)C)(C)C.[O-]O.C1(C(C)C)C=CC=CC=1>C1(C)C=CC=CC=1.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH3:16][C:17]1[C:18]([CH2:29][S:30]([C:31]2[NH:32][C:33]3[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=3[N:35]=2)=[O:3])=[N:19][CH:20]=[CH:21][C:22]=1[O:23][CH2:24][C:25]([F:27])([F:26])[F:28]Participants
Conditions
- Temperature
- 50 °C
Procedure
For example, in Example 22 of this publication, it is described that a mixture, which was obtained by adding water (3.6 mmol), (+)-diethyl L-tartrate (15.0 mmol) and titanium(IV) isopropoxide (6.0 mmol) to a solution of 2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]thio]-1H-benzimidazole (6.0 mmol) in toluene, stirring the resulting mixture at 50° C. for 60 min, cooling the reaction mixture to room temperature, adding N,N-diisopropylethylamine (6.0 mmol) and cumene hydroperoxide (6.0 mmol) and stirring the mixture at room temperature for 16 hr, consisted of 13% of sulfide, 8% of sulfone and 76% of sulfoxide as determined by achiral HPLC, that post-treatments of purification by flash chromatography and the like gave (+)-2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazole (0.85 g) showing 46%ee enantiomer excess, and that, by further purification, 0.31 g (14%) of the objective substance having an optical purity of 99.6%ee was ultimately obtained as an oily substance.
Workup
- customwhich was obtained
- temperaturecooling the reaction mixture to room temperature
- stirringstirring the mixture at room temperature for 16 hr
- customthat post-treatments of purification by flash chromatography
Sources & evidence
- ORD record
- ord-64d384293e6b40058f093c474bf23b69
- Source dataset
- uspto-grants-2006_01
- Patent number
- US06982275B2
Reaction notes
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