(r)-Omeprazole

Base Information

• Chemical Name: (r)-Omeprazole
• CAS No.: 119141-89-8
• Deprecated CAS: 177541-02-5
• Molecular Formula: C17H19N3O3S
• Molecular Weight: 345.422
• Hs Code.: 2941500000
• European Community (EC) Number: 643-098-6
• UNII: S51HU491WJ
• DSSTox Substance ID: DTXSID401317408
• Wikipedia: Esomeprazole
• Wikidata: Q27146846
• NCI Thesaurus Code: C65538,C65539
• RXCUI: 283742,1294569
• Metabolomics Workbench ID: 43040
• ChEMBL ID: CHEMBL4117512
• Mol file: 119141-89-8.mol

Synonyms:Esomeprazole;Esomeprazole Magnesium;Esomeprazole Potassium;Esomeprazole Sodium;Esomeprazole Strontium;Esomeprazole Strontium Anhydrous;Nexium;Strontium, Esomeprazole

Chemical Property of (r)-Omeprazole

Chemical Property:

• Appearance/Colour: white solid
• Boiling Point: 600 °C at 760 mmHg
• PKA: 8.78±0.10(Predicted)
• Flash Point: 316.7 °C
• PSA: 96.31000
• Density: 1.37 g/cm³
• LogP: 3.76540
• Storage Temp.: 2-8°C
• Solubility.: H2O: 0.5 mg/mL
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 345.11471265
• Heavy Atom Count: 24
• Complexity: 453

Purity/Quality:

99% ^*data from raw suppliers

(R)-Omeprazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN=C(C(=C1OC)C)CS(=O)C2=NC3=C(N2)C=C(C=C3)OC
• Isomeric SMILES: CC1=CN=C(C(=C1OC)C)C[S@@](=O)C2=NC3=C(N2)C=C(C=C3)OC
• Recent ClinicalTrials: A Study to Evaluate the Efficacy and Safety of Tegoprazan in GERD Patients With Nighttime Heartburn
• Recent EU Clinical Trials: 'A Phase III Study to Assess the Efficacy and Safety of NEXIUM for Maintenance of Healing of Erosive Esophagitis in Pediatric Patients 1 to 11 Years of Age'
• Recent NIPH Clinical Trials: V-POINT study
• Uses: R-Form of Omeprazole. Gastric proton-pump inhibitor (R)-Omeprazole is the R-enantiomer of Omeprazole (O635000), which binds covalently to proton pump. It inhibits gastric secretion. Used as an anttiulcerative.

Technology Process of (r)-Omeprazole

There total 16 articles about (r)-Omeprazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.5%

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

Guidance literature:

With C₆₈H₇₂N₄O₁₀Ti₂; dihydrogen peroxide; In water; ethyl acetate; at 0 ℃; for 24h; Reagent/catalyst; enantioselective reaction;

DOI:10.1016/j.cattod.2016.03.006

Reference yield: 82.0%

6-methoxy-2-(((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)thio)-1H-benzo[d]imidazole (73590-85-9) → (S)-6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]-sulfinyl]-1H-benzimidazole (119141-88-7,326602-80-6) + (R)-6-methoxy-2-((4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl)-1H-benzoimidazole (119141-89-8,326602-80-6)

Guidance literature:

6-methoxy-2-(((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)thio)-1H-benzo[d]imidazole; With bis(acetylacetonate)oxovanadium; C₂₂H₃₃NO₂; N-ethyl-N,N-diisopropylamine; at 0 - 5 ℃;

With Cumene hydroperoxide; In Isopropylbenzene; for 6h; optical yield given as %ee;

DOI:10.1007/s11172-008-0221-6

Reference yield: 80.0%

→ (S)-6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]-sulfinyl]-1H-benzimidazole (119141-88-7,326602-80-6) + (R)-6-methoxy-2-((4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl)-1H-benzoimidazole (119141-89-8,326602-80-6)

Guidance literature:

With dihydrogen peroxide; In water; at 25 ℃; stereoselective reaction;

upstream raw materials:

omeprazole

1-(S)-camphor sulfonyl-6-methoxy-2-[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl-(R)-sulfinyl]-1H-benzimidazole

omeprazole sulfide

6-methoxy-2-(((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)thio)-1H-benzo[d]imidazole

Refernces

• 1、 Zhang, Yuanyuan,Lv, Kuiying,Deng, Yashan,Li, Huiling,Wang, Zhiyong,Li, Depeng,Gao, Xin,Wang, Fanye. "Asymmetric Bio-oxidation Using Resting Cells of Rhodococcus rhodochrous ATCC 4276 Mutant QZ-3 for Preparation of (S)-Omeprazole in a Chloroform–Water Biphasic System Using Response Surface Methodology". . p. 2928 - 2938. Retrieved 2021/02/01.
• 2、 Nosek, Vladimír,Mí?ek, Ji?í. "Enzymatic kinetic resolution of chiral sulfoxides-an enantiocomplementary approach". supporting information. p. 10480 - 10483. Retrieved 2019/09/07.