(R)-(+)-Pantoprazole

Base Information

• Chemical Name: (R)-(+)-Pantoprazole
• CAS No.: 142706-18-1
• Molecular Formula: C16H15F2N3O4S
• Molecular Weight: 383.37000
• UNII: 8UUN42B3QT
• ChEMBL ID: CHEMBL2096747
• Mol file: 142706-18-1.mol

Synonyms:(R)-(+)-Pantoprazole;142706-18-1;R-Pantoprazole;(+)-Pantoprazole;Pantoprazole, (R)-;8UUN42B3QT;CHEMBL2096747;6-(difluoromethoxy)-2-[(R)-(3,4-dimethoxypyridin-2-yl)methylsulfinyl]-1H-benzimidazole;1H-Benzimidazole, 5-(difluoromethoxy)-2-((R)-((3,4-dimethoxy-2-pyridinyl)methyl)sulfinyl)-;1H-Benzimidazole, 6-(difluoromethoxy)-2-((R)-((3,4-dimethoxy-2-pyridinyl)methyl)sulfinyl)-;6-(Difluoromethoxy)-2-((R)-((3,4-dimethoxy-2-pyridinyl)methyl)sulfinyl)-1H-benzimidazole;1H-Benzimidazole, 5-(difluoromethoxy)-2-(((3,4-dimethoxy-2-pyridinyl)methyl)sulfinyl)-, (+)-;UNII-8UUN42B3QT;SCHEMBL22198;IQPSEEYGBUAQFF-AREMUKBSSA-N;BDBM50409893;CS-T-38666;PD132312

Chemical Property of (R)-(+)-Pantoprazole

Chemical Property:

• Melting Point: >145oC (dec.)
• Boiling Point: 586.9±60.0 °C(Predicted)
• PKA: 8.33±0.10(Predicted)
• PSA: 105.54000
• Density: 1.51±0.1 g/cm3(Predicted)
• LogP: 3.75000
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 7
• Exact Mass: 383.07513347
• Heavy Atom Count: 26
• Complexity: 490

Purity/Quality:

99%min ^*data from raw suppliers

(R)-(+)-Pantoprazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C(=NC=C1)CS(=O)C2=NC3=C(N2)C=C(C=C3)OC(F)F)OC
• Isomeric SMILES: COC1=C(C(=NC=C1)C[S@@](=O)C2=NC3=C(N2)C=C(C=C3)OC(F)F)OC
• Uses: (R)-(+)-Pantoprazole is the R-enantiomer of Pantoprazole (P183000), an antiulcerative. Gastric pump inhibitor.

Technology Process of (R)-(+)-Pantoprazole

There total 4 articles about (R)-(+)-Pantoprazole 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: 75.0%

5-difluoromethoxy-2-[[(3,4-dimethoxy-2-pyridyl)methyl]sulfanyl]-1H-benzimidazole → (S)-5-difluoromethoxy-2-[[(3,4-dimethoxy-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole (142678-35-1) + ((R)-6-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methylsulfinyl]-1H-benzo[d]imidazole) (142706-18-1)

Guidance literature:

With lithium 4-dimethylaminobenzoate; iron(III)-acetylacetonate; C₁₃H₁₇Cl₂NO₂; dihydrogen peroxide; In water; ethyl acetate; at -15 - -6 ℃; enantioselective reaction;

DOI:10.1021/acscatal.8b02610

Reference yield: 49.0%

pantoprazole sulfide (102625-64-9) → ((R)-6-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methylsulfinyl]-1H-benzo[d]imidazole) (142706-18-1)

Guidance literature:

pantoprazole sulfide; With titanium(IV) isopropylate; D-tartaric acid; at -5 ℃; for 1h;

With bis(1-methylethyl)phenyl hydroperoxide; N-ethyl-N,N-diisopropylamine; at -5 - 0 ℃; for 24h; Darkness;

Reference yield:

pantoprazole → (S)-5-difluoromethoxy-2-[[(3,4-dimethoxy-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole (142678-35-1) + ((R)-6-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methylsulfinyl]-1H-benzo[d]imidazole) (142706-18-1)

Guidance literature:

With hydroxypropyl-β-cyclodextrin; In 1,2-dichloro-ethane; at 5 ℃; for 12h; pH=8.5; Reagent/catalyst; Temperature; Solvent; pH-value; Concentration; enantioselective reaction; Resolution of racemate;

DOI:10.2478/s11696-013-0501-y

upstream raw materials:

5-(difluoromethoxy)-2-mercapto-1H-benzimidazole

pantoprazole sulfide

Refernces

• 1、 -. "Method for preparing high-purity razole intermediate and medicine by using green technology instead of phosgene, thionyl chloride and other toxic and harmful substances". . . Retrieved 2017/09/01.