119141-89-8

Basic information

• Product Name: OMEPRAZOLE
• Synonyms: ZOLTUM;R-(+)-OMEPRAZOLE;(S)-OMEPRAZOLE;OMEPRAL;PRILOSEC;MOPRAL;MEPRAL;LOSEC
• CAS NO: 119141-89-8
• Molecular Formula: C₁₇H₁₉N₃O₃S
• Molecular Weight: 345.42
• EINECS: 201-212-8
• Product Categories: Chiral Reagents;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 119141-89-8.mol
• Article Data: 41

Chemical Properties

• Boiling Point: 600 °C at 760 mmHg
• Flash Point: 316.7 °C
• Appearance: white/solid
• Density: 1.37±0.1 g/cm3 (20 ºC 760 Torr)
• Storage Temp.: 2-8°C
• Solubility: H2O: 0.5 mg/mL
• PKA: 8.78±0.10(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: OMEPRAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: OMEPRAZOLE(119141-89-8)
• EPA Substance Registry System: OMEPRAZOLE(119141-89-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: DD9087000
• Hazardous Substances Data: 119141-89-8(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 119141-89-8 differently. You can refer to the following data:
1. R-Form of Omeprazole. Gastric proton-pump inhibitor
2. (R)-Omeprazole is the R-enantiomer of Omeprazole (O635000), which binds covalently to proton pump. It inhibits gastric secretion. Used as an anttiulcerative.

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.

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)

Synthetic route

omeprazole sulfide (73590-85-9) → (R)-omeprazole (119141-89-8)

Conditions	Yield
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 (73590-58-6) → (R)-omeprazole (119141-89-8)

Conditions	Yield
enantiomeric resolution; inclusion complexation with (R)-(+)-2,2'-dihydroxy-1,1'-binaphthyl;

omeprazole sodium → (R)-omeprazole (119141-89-8)

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;

omeprazole (73590-58-6) → (R)-omeprazole (119141-89-8) + esomeprazole (119141-88-7)

Conditions	Yield
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-(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 (1138242-22-4) + 1-(S)-camphor sulfonyl-5-methoxy-2-[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl-(R)-sulfinyl]-1H-benzimidazole → (R)-omeprazole (119141-89-8)

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;

omeprazole sulfide (73590-85-9) → (R)-omeprazole (119141-89-8) + esomeprazole (119141-88-7)

Conditions	Yield
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.;

omeprazole sulfide (73590-85-9) → (R)-omeprazole (119141-89-8) + omeprazole sulphone + esomeprazole (119141-88-7)

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

3C8H8O3*C8H14O6*C12H28O4Ti*C17H19N3O3S → (R)-omeprazole (119141-89-8)

Conditions	Yield
With sodium hydrogencarbonate In dichloromethane; water at 20℃; for 0.5h; Product distribution / selectivity;

1-(S)-camphor sulfonyl-5-methoxy-2-[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl-(R/S)-sulfinyl]-1H-benzimidazole → (R)-omeprazole (119141-89-8) + esomeprazole (119141-88-7)

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;

omeprazole sodium → (R)-omeprazole (119141-89-8) + esomeprazole (119141-88-7)

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

(R)-omeprazole (119141-89-8) → 5-methoxy-2-[(R)-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole sodium salt

Conditions	Yield
With sodium hydroxide In methanol at 20℃; for 0.5h;	95%
With sodium hydroxide In methanol at 5 - 10℃; for 0.75 - 1.5h;

(R)-omeprazole (119141-89-8) → (R)-esomeprazole potassium salt

Conditions	Yield
With potassium hydroxide In methanol at 20℃; for 0.5h; Product distribution / selectivity;	94.1%
With potassium hydroxide In methanol at 5 - 10℃; for 0.75 - 1.5h;

(R)-omeprazole (119141-89-8) → esomeprazole magnesium dihydrate

Conditions	Yield
With magnesium chloride In methanol; water at 20℃; for 0.5h;	90%

chloromethyl (1R)-endo-(+)-fenchyl ether + (R)-omeprazole (119141-89-8) → 5-Methoxy-2-((R)-4-methoxy-3,5-dimethyl-pyridin-2-ylmethanesulfinyl)-1-((1R,2R,4S)-1,3,3-trimethyl-bicyclo[2.2.1]hept-2-yloxymethyl)-1H-benzoimidazole + 6-methoxy-2-{[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]-(R)-sulfinyl}-1-({[(1R-endo)-1,3,3-trimethylbicyclo[2.2.1]hept-=2-yl]oxy}methyl)-1H-benzimidazole

(R)-omeprazole (119141-89-8) → (-)-5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulphinyl]-1H-benzimidazole magnesium

Conditions	Yield
Stage #1: With magnesium In methanol; dichloromethane for 1 - 2h; Stage #2: (R)-omeprazole In methanol; dichloromethane at 5 - 10℃; for 0.25 - 0.5h;

(R)-omeprazole (119141-89-8) → magnesium R-omeprazole

Conditions	Yield
Stage #1: (R)-omeprazole With magnesium ethylate In methanol; ethanol for 48h; Stage #2: With water In methanol for 1h;

(R)-omeprazole (119141-89-8) → S-omeprazole magnesium

Conditions	Yield
With magnesium methanolate In methanol at 20℃; for 0.5h;	n/a

Upstream product

• 73590-85-9 omeprazole sulfide 
• 113713-24-9 5-methoxy-2-((4-methoxy-3,5-dimethylpyridin-2-yl)methylthio)-1H-imidazo[4,5-b]pyridine 
• 1138242-22-4 1-(S)-camphor sulfonyl-6-methoxy-2-[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl-(R)-sulfinyl]-1H-benzimidazole 
• 73590-58-6 omeprazole 
• 73590-58-6 omeprazole 
• 73590-85-9 6-methoxy-2-(((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)thio)-1H-benzo[d]imidazole 

Relevant articles and documents

An efficient asymmetric approach to the R-enantiomer impurity of esomeprazole

Esomeprazole {(S)-5-methoxy-2-[(4-methoxy-3, 5-dimethyl-2-pyridinylmethyl) sulfinyl]-1H-benzimidazole} is a proton pump inhibitor used as an antiulcer drug. Its R-enantiomer 3 was synthesized with high enantioselectivity by asymmetric oxidation of prochiral sulfide 2 using the oxaziridinium salt 4. Product 3, useful as a reference for the quality control of esomeprazole, was characterized by 1H and 13C NMR, IR, and HRMS. The enantiomeric excess was determined by HPLC.

Method for preparing chiral sulfoxide drugs in water phase

The invention relates to the field of chiral drug preparation, in particular to a method for preparing chiral sulfoxide drugs in a water phase. The method for preparing the chiral sulfoxide drugs in the water phase comprises the following steps: using a hydrogen peroxide solution as oxidant, using a temperature-sensitive ferrocene chiral amino acid titanium complex as a catalyst and using prochiral thioether as a substrate in the pure water phase to perform an asymmetric oxidation reaction to synthesize the chiral sulfoxide drugs. The temperature-sensitive ferrocene chiral amino acid titaniumcomplex catalyst can be utilized to catalyze the asymmetric oxidation reaction of thioether in the pure water phase and has the characteristics of high catalytic efficiency and easy recovery of the catalyst.

Method for producing proton pump inhibitor compound having optical activity

A highly pure optically active proton pump inhibitor compound can be produced safely and inexpensively in a high yield and enantioselectivity by a method of producing an optically active sulfoxide of Formula 2 or a salt thereof, comprising oxidizing a sulfide of Formula 1 or a salt thereof with hydrogen peroxide using an iron salt in the presence of a chiral ligand of Formula 3; wherein A is CH or N; R1 is hydrogen atom, an alkyl optionally substituted by halogen(s), or an alkoxy optionally substituted by halogen(s); one to three R2 may exist, and each of R2 is independently an alkyl, a dialkylamino, or an alkoxy optionally substituted by halogen(s) or alkoxy(s); each of R3 is independently hydrogen atom, a halogen, cyano or the like; R4 is a tertiary alkyl; and * and ** represent respectively R configuration or S configuration.