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CAS No.: | 119141-89-8 |
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Name: | OMEPRAZOLE |
Article Data: | 41 |
Molecular Structure: | |
Formula: | C17H19N3O3S |
Molecular Weight: | 345.422 |
Synonyms: | 1H-Benzimidazole,5-methoxy-2-[(R)-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]- (9CI);1H-Benzimidazole-1-acetic acid,5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-, (+)-;(+)-Omeprazole;(R)-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;(R)-Esomeprazole;1H-Benzimidazole,5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-, (R)-;(R)-Omeprazole; |
EINECS: | 201-212-8 |
Density: | 1.37 g/cm3 |
Boiling Point: | 600 °C at 760 mmHg |
Flash Point: | 316.7 °C |
Solubility: | H2O: 0.5 mg/mL |
Appearance: | white solid |
Hazard Symbols: | Xi |
Risk Codes: | 36/37/38 |
Safety: | 26-36 |
PSA: | 96.31000 |
LogP: | 3.76540 |
omeprazole sulfide
(R)-omeprazole
Conditions | Yield |
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With C68H72N4O10Ti2; dihydrogen peroxide In water; ethyl acetate at 0℃; for 24h; Reagent/catalyst; enantioselective reaction; | 93.5% |
With N-methyl-6-aza-5β,6β-epoxy-cholestane-3β-tert-butyldiphenylsilyloxy tetrafluoroborate In dichloromethane at -70 - 20℃; for 3h; Inert atmosphere; enantioselective reaction; | 86% |
With tert.-butylhydroperoxide In water; toluene at -20℃; for 12h; | n/a |
omeprazole
(R)-omeprazole
Conditions | Yield |
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enantiomeric resolution; inclusion complexation with (R)-(+)-2,2'-dihydroxy-1,1'-binaphthyl; |
(R)-omeprazole
Conditions | Yield |
---|---|
Stage #1: omeprazole sodium With diethyl (2S,3S)-tartrate; (S)-Mandelic acid; titanium(IV)isopropoxide; triethylamine In acetone at 35 - 40℃; for 0.25 - 0.5h; Stage #2: With sodium hydrogencarbonate In dichloromethane for 0.25 - 0.5h; |
Conditions | Yield |
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With triethylamine In methanol Purification / work up; Chiral supercritical fluid chromatography; Resolution of racemate; | |
With N,N-dimethyl-ethanamine In ethanol Purification / work up; Chiral supercritical fluid chromatography; Resolution of racemate; | |
With N,N-dimethyl-ethanamine In methanol Purification / work up; Chiral supercritical fluid chromatography; Resolution of racemate; |
1-(S)-camphor sulfonyl-6-methoxy-2-[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl-(R)-sulfinyl]-1H-benzimidazole
(R)-omeprazole
Conditions | Yield |
---|---|
Stage #1: 1-(S)-camphor sulfonyl-6-methoxy-2-[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl-(S)-sulfinyl]-1H-benzimidazole; 1-(S)-camphor sulfonyl-5-methoxy-2-[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl-(S)-sulfinyl]-1H-benzimidazole; 1-(S)-camphor sulfonyl-6-methoxy-2-[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl-(R)-sulfinyl]-1H-benzimidazole; 1-(S)-camphor sulfonyl-5-methoxy-2-[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl-(R)-sulfinyl]-1H-benzimidazole With methanol at 25℃; for 0.5h; Stage #2: With methanol; sodium hydroxide; water at 25℃; for 3.16667h; Stage #3: With water; acetic acid In methanol pH=6.8; |
Conditions | Yield |
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With 1,2:4,5-di-O-cyclohexylidene-D-fructopyranose; Cumene hydroperoxide; vanadium(V) oxytripropoxide; N-ethyl-N,N-diisopropylamine In water; ethyl acetate at 20 - 55℃; for 20.1667 - 20.25h; Product distribution / selectivity; | |
With Oxone; ethylenediaminetetraacetic acid; sodium hydrogencarbonate; 1,2:4,5-di-O-cyclohexylidene-β-D-erythro-hexo-2,3-diulopyranose In acetonitrile at -10 - 20℃; for 3.16667 - 3.25h; Product distribution / selectivity; | |
Stage #1: omeprazole sulfide With diethyl (2S,3S)-tartrate; titanium(IV) isopropylate In water; toluene at 55℃; for 1h; Stage #2: With Cumene hydroperoxide In water; toluene at 30℃; for 4.5h; Further stages. Title compound not separated from byproducts.; |
Conditions | Yield |
---|---|
Stage #1: omeprazole sulfide With titanium(IV) isopropylate; diethyl (2S,3S)-tartrate In water at 20 - 70℃; for 1.5h; Heating / reflux; Stage #2: With Cumene hydroperoxide In water at 20℃; Product distribution / selectivity; | |
Stage #1: omeprazole sulfide With titanium(IV) isopropylate; diethyl (2S,3S)-tartrate In dichloromethane; water at 20 - 70℃; for 1.5h; Heating / reflux; Stage #2: With Cumene hydroperoxide In dichloromethane; water at 20℃; Product distribution / selectivity; | |
With dihydrogen peroxide; Mn-complex of (R,R)-1,2-bis(3,5-di-tert-butyl-2-hydroxybenzylamino)cyclohexane In water; acetonitrile at -10℃; for 5h; Product distribution / selectivity; | A n/a B n/a C n/a |
(R)-omeprazole
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In dichloromethane; water at 20℃; for 0.5h; Product distribution / selectivity; |
Conditions | Yield |
---|---|
Stage #1: 1-(S)-camphor sulfonyl-5-methoxy-2-[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl-(R/S)-sulfinyl]-1H-benzimidazole With water; sodium hydroxide at 25℃; for 6.5h; Stage #2: With hydrogenchloride In dichloromethane; water pH=7.0; Product distribution / selectivity; |
Conditions | Yield |
---|---|
Stage #1: omeprazole sodium With titanium(IV) isopropylate; diethyl (2S,3S)-tartrate; water; triethylamine In acetone at 35 - 40℃; Stage #2: With (S)-Mandelic acid In acetone at 35 - 40℃; for 2h; Stage #3: With sodium hydrogencarbonate In dichloromethane; water for 0.5h; Concentration; | A n/a B n/a |
The 1H-Benzimidazole,6-methoxy-2-[(R)-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]- is an organioc compound with the formula C17H19N3O3S. The IUPAC name of this chemical is 6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1H-benzimidazole. With the CAS registry number 119141-89-8, it is also named as Omeprazole. The product's categories are Chiral Reagents; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals. It is white solid.
The other characteristics of 1H-Benzimidazole,6-methoxy-2-[(R)-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]- can be summarized as: (1)ACD/LogP: 2.17; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.11; (4)ACD/LogD (pH 7.4): 2.17; (5)ACD/BCF (pH 5.5): 22.95; (6)ACD/BCF (pH 7.4): 26.19; (7)ACD/KOC (pH 5.5): 315.1; (8)ACD/KOC (pH 7.4): 359.55; (9)#H bond acceptors: 6; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 85.45 Å2; (13)Index of Refraction: 1.669; (14)Molar Refractivity: 94.02 cm3; (15)Molar Volume: 251.8 cm3; (16)Surface Tension: 75.1 dyne/cm; (17)Enthalpy of Vaporization: 89.31 kJ/mol; (18)Vapour Pressure: 2.35E-14 mmHg at 25°C; (19)Rotatable Bond Count: 5; (20)Tautomer Count: 2; (21)Exact Mass: 345.114712; (22)MonoIsotopic Mass: 345.114712; (23)Topological Polar Surface Area: 96.3; (24)Heavy Atom Count: 24; (25)Complexity: 453.
When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.
People can use the following data to convert to the molecule structure.
1. SMILES:O=S(c2nc1ccc(OC)cc1n2)Cc3ncc(c(OC)c3C)C
2. InChI:InChI=1/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)
3. InChIKey:SUBDBMMJDZJVOS-UHFFFAOYAZ