| Identification | Back Directory | [Name]
OMEPRAZOLE | [CAS]
119141-89-8 | [Synonyms]
LOSEC
ANTRA
ZOLTUM
MEPRAL
MOPRAL
OMEPRAL
PRILOSEC
H 168/68
GASTROLOC
GASTROGARD
R-Omeparazole
(S)-OMEPRAZOLE
R-(+)-OMEPRAZOLE
Omeprazole R-Isomer
Omeprazole Impurity N
Omeprazole Impurity 33
EsoMeprazole iMpurity F
Erythromycine Thiocynate
Esomeprazole EP Impurity F
Esomeprazole Sodium Impurity 15
omeprazole impurity B (r-omeprazole)
Omeprazole impurity N (R)-Omeprazole
2-[(4-METHOXY-3,5-DIMETHYLPYRID-2-YL)-METHYLSULFO]-5-METHOXYBENZIMIDAZOLE
5-METHOXY-2[(4-METHOXY-3,5-DIMETHYL-2-PYRIDYL)METHYLSULFINYL]-1H-BENZIMIDAZOLE
5-METHOXY-2-[[(4-METHOXY-3,5-DIMETHYL-2-PYRIDINYL)METHYL]SULFINYL]-1H-BENZIMIDAZOLE
(R)-5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole
6-methoxy-2-[(R)-(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1H-benzimidazole
(R)-6-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole
5-Methoxy-2-[(R)-[(4-Methoxy-3,5-diMethylpyridin-2-yl)Methyl]sulfinyl]-1H-benziMidazole
6-Methoxy-2-[(R)-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole
1H-BenziMidazole,6-Methoxy-2-[(R)-[(4-Methoxy-3,5-diMethyl-2-pyridinyl)Methyl]sulfinyl]-
Omeprazole impurity 18/(R)-Omeprazole/(R)-5-Methoxy-2-(((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)sulfinyl)-1H-benzo[d]imidazole | [EINECS(EC#)]
201-212-8 | [Molecular Formula]
C17H19N3O3S | [MDL Number]
MFCD00083192 | [MOL File]
119141-89-8.mol | [Molecular Weight]
345.42 |
| Chemical Properties | Back Directory | [Melting point ]
>47°C (dec.) | [Boiling point ]
600.0±60.0 °C(Predicted) | [density ]
1.37±0.1 g/cm3 (20 ºC 760 Torr) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
H2O: 0.5 mg/mL
| [form ]
solid
| [pka]
8.78±0.10(Predicted) | [color ]
white
| [Stability:]
Hygroscopic | [InChI]
InChI=1S/C17H19N3O3S/c1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20)/t24-/m1/s1 | [InChIKey]
SUBDBMMJDZJVOS-XMMPIXPASA-N | [SMILES]
C1([S@@](CC2=NC=C(C)C(OC)=C2C)=O)NC2=CC(OC)=CC=C2N=1 |
| Hazard Information | Back Directory | [Uses]
R-Form of Omeprazole. Gastric proton-pump inhibitor | [Definition]
ChEBI: A 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole that has R configuration at the sulfur atom. | [Synthesis]
GENERAL STEPS: Sulfide (5-methoxy-2-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]thio]benzimidazole, 100 mmol) and titanium-tannic acid catalyst (1.1 mmol) were dissolved in ethyl acetate (EtOAc, 6.0 mL). The reaction mixture was kept at a constant temperature to the indicated temperature (usually 0°C, or in the range of -20 to +20°C for variable temperature experiments). Subsequently, a 30% aqueous hydrogen peroxide solution (0.105 mmol H2O2) was added all at once. The reaction mixture was continuously stirred at 500 rpm at a constant temperature (usually 24 h). For low-temperature experiments, the reaction time was about 30 h at -10 °C, which could be extended to 10 days at -20 °C. To analyze the progress of the reaction, 20 μL of the reaction mixture was taken into a vial and immediately evaporated carefully to dryness (~15-20 s) with a stream of compressed air. The residual solid was dissolved in isopropanol solution (0.20 mL) containing 1% triethylamine (Et3N), and the residual sulfide, (R)- and (S)-sulfoxide, and sulfone contents were analyzed by chiral HPLC. | [References]
[1] Catalysis Today, 2017, vol. 279, p. 84 - 89
[2] Heterocyclic Communications, 2016, vol. 22, # 1, p. 17 - 19
[3] Patent: US2008/319195, 2008, A1. Location in patent: Page/Page column 5
[4] Patent: US9228216, 2016, B2. Location in patent: Page/Page column 50-52
[5] Journal of Organic Chemistry, 2018, vol. 83, # 14, p. 7453 - 7458 |
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