tert-Butyl hydroperoxide → Tenatoprazole

HRID 490959Notes

Reaction equation

HRID 490959 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]2[N:9]=[C:10]([S:12][CH2:13][C:14]3[C:19]([CH3:20])=[C:18]([O:21][CH3:22])[C:17]([CH3:23])=[CH:16][N:15]=3)[NH:11][C:6]2=[CH:5][CH:4]=1.[O-]O.C1(C(C)C)C=CC=CC=1.C([O:39]O)(C)(C)C.NC1(O)C2C(=CC=CC=2)CC1>CN1C(=O)CCC1.CC(O[Ti](OC(C)C)(OC(C)C)OC(C)C)C>[CH3:1][O:2][C:3]1[N:8]=[C:7]2[N:9]=[C:10]([S:12]([CH2:13][C:14]3[C:19]([CH3:20])=[C:18]([O:21][CH3:22])[C:17]([CH3:23])=[CH:16][N:15]=3)=[O:39])[NH:11][C:6]2=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 6410tert-Butyl hydroperoxideHCID 98404895-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]thio]-1H-imidazo[4,5b]pyridineHCID 19357388AminoindanolHCID 53627471Cumen hydroperoxide

Product 1

HCID 636411Tenatoprazole

Reagents, catalysts & solvents 2

HCID 178460666HCID 178460666, compoundCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Therefore, for example, according to the method of the invention, an enantioselective oxidation of 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]thio]imidazo[4,5-b]-pyridine by cumene hydroperoxide or tert-butyl hydroperoxide in presence of Ti(OiPr)4 and of amino-indanol in NMP can advantageously be carried out in order to obtain (−)-5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]imidazo[4,5-b]pyridine, that is to say tenatoprazole, the formula of which is represented above.

Sources & evidence

ORD record
ord-3a0e21eab0444bd4b6ec67d8f1327587
Source dataset
uspto-grants-2009_05
Patent number
US07528251B2

Reaction notes

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