Levolansoprazole

Base Information

• Chemical Name: Levolansoprazole
• CAS No.: 138530-95-7
• Deprecated CAS: 1336907-94-8
• Molecular Formula: C16H14 F3 N3 O2 S
• Molecular Weight: 369.367
• UNII: FB55O16184
• DSSTox Substance ID: DTXSID70160706
• Wikidata: Q27277903
• NCI Thesaurus Code: C170116
• Mol file: 138530-95-7.mol

Synonyms:Levolansoprazole;(S)-Lansoprazole;138530-95-7;(-)-Lansoprazole;Levolansoprazole [INN];(S)-2-(((3-Methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methyl)sulfinyl)-1H-benzo[d]imidazole;UNII-FB55O16184;FB55O16184;LANSOPRAZOLE, (S)-;SCHEMBL22366;DTXSID70160706;2-[(S)-[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl]-1H-benzimidazole;(-)-Lansoprazole(S)-Lansoprazole;AKOS027383932;SB48823;2-[(S)-[[3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazole;AC-30441;CS-0090353;J-007155;Q27277903;(S)-2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazole;2-({[3-methyl-4-(2,2,2-trifluroethoxy)-2-pyridinyl]methyl}- sulfinyl)-1H-benzimidazole;2-[(S)-[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methylsulfinyl]-1H-benzimidazole;(-)-2-((S)-((3-METHYL-4-(2,2,2-TRIFLUOROETHOXY)PYRIDIN-2-YL)METHYL)SULFINYL)-1H-BENZAMIDAZOLE

Chemical Property of Levolansoprazole

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 60-65°C
• Boiling Point: 555.8°Cat760mmHg
• PKA: 9.56±0.10(Predicted)
• Flash Point: 289.9°C
• PSA: 87.08000
• Density: 1.5g/cm³
• LogP: 4.38090
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 369.07588236
• Heavy Atom Count: 25
• Complexity: 480

Purity/Quality:

99% ^*data from raw suppliers

(S)-Lansoprazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=CN=C1CS(=O)C2=NC3=CC=CC=C3N2)OCC(F)(F)F
• Isomeric SMILES: CC1=C(C=CN=C1C[S@](=O)C2=NC3=CC=CC=C3N2)OCC(F)(F)F
• Description: (S)-Lansoprazole is a proton pump inhibitor that irreversibly inhibits H+/K+-stimulated ATPase pumps in parietal cells (IC50 = 5.2 μM), inhibiting gastric acid secretion and increasing intragastric pH. It also inhibits acid formation in isolated canine parietal cells (IC50 = 82 μM). (S)-Lansoprazole is an enantiomerically pure form of lansoprazole . Both (S)- and (R)-lansoprazole are pharmacologically active with similar potencies.
• Uses: The S-enantiomer of Lansoprazole; a gastric proton pump inhibitor. An antiulcerative. The S-enantiomer of Lansoprazole; a gastric proton pump inhibitor. An antiulcerative

Technology Process of Levolansoprazole

There total 12 articles about Levolansoprazole 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: 96.0%

lansoprazole sulfide (103577-40-8) → (S)-lansoprazole (138530-95-7)

Guidance literature:

With sodium dihydrogenphosphate; 1,4-bis((4S,5S)-1,3-bis(3,5-di-tert-butylbenzyl)-4,5-diphenylimidazolidin-2-ylidene)piperazine-1,4-diium dichloride; O₄W^(2-)*Ag⁽²⁺⁾; dihydrogen peroxide; at 5 ℃; for 48h; enantioselective reaction;

DOI:10.1002/anie.201601574

Reference yield: 90.0%

(S)-(-)-2-(3-methyl-4-nitropyridin-2-ylmethansulfinyl)-1H-benzimidazole (142384-07-4) + 2,2,2-trifluoroethanol (75-89-8) → (S)-lansoprazole (138530-95-7)

Guidance literature:

With potassium tert-butylate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; at 80 ℃; for 4h; Product distribution / selectivity;

Reference yield: 89.0%

→ (S)-lansoprazole (138530-95-7)

Guidance literature:

With manganese(II) triflate; C₃₀H₃₄N₄O₂; dihydrogen peroxide; acetic acid; In dichloromethane; at 0 ℃; for 1h;

upstream raw materials:

lansoprazole sulfide

(S)-(-)-2-(3-methyl-4-nitropyridin-2-ylmethansulfinyl)-1H-benzimidazole

2,2,2-trifluoroethanol

lansoprasole

Downstream raw materials:

isopropyl 1-[(S)-2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazol-l-yl] ethyl carbonate

Refernces

• 1、 -. "Method for preparing chiral sulfoxide drugs in water phase". Paragraph 0050-0052. . Retrieved 2020/09/09.
• 2、 -. "Method for producing proton pump inhibitor compound having optical activity". Page/Page column 15; 16. . Retrieved 2019/06/15.