[5-(4-Amino-2-oxopyrimidin-1-yl)-1,3-oxathiolan-2-yl]methyl 2-hydroxybenzoate

Base Information

• Chemical Name: [5-(4-Amino-2-oxopyrimidin-1-yl)-1,3-oxathiolan-2-yl]methyl 2-hydroxybenzoate
• CAS No.: 173522-96-8
• Molecular Formula: C8H11N3O3S^.C7H6O3
• Molecular Weight: 367.382
• European Community (EC) Number: 827-409-4
• Mol file: 173522-96-8.mol

Synonyms:173522-96-8;SB48929

Chemical Property of [5-(4-Amino-2-oxopyrimidin-1-yl)-1,3-oxathiolan-2-yl]methyl 2-hydroxybenzoate

Chemical Property:

• PSA: 173.20000
• LogP: 1.07750
• Storage Temp.: 2-8°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 349.07324176
• Heavy Atom Count: 24
• Complexity: 567

Purity/Quality:

99% ^*data from raw suppliers

LamivudineSalicylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(OC(S1)COC(=O)C2=CC=CC=C2O)N3C=CC(=NC3=O)N
• Uses: Lamivudine Salicylate is used in method for low-cost synthesis of Lamivudine Antiviral drug.Lamivudine and its pharmaceutical salts used for treating age-related macular degeneration.

Technology Process of [5-(4-Amino-2-oxopyrimidin-1-yl)-1,3-oxathiolan-2-yl]methyl 2-hydroxybenzoate

There total 3 articles about [5-(4-Amino-2-oxopyrimidin-1-yl)-1,3-oxathiolan-2-yl]methyl 2-hydroxybenzoate 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: 91.04%

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathiolane-2-carboxylate (147027-10-9,147126-73-6,147126-74-7,147126-80-5) → lamivudine salicyclic acid salt (173522-96-8)

Guidance literature:

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathiolane-2-carboxylate; With potassium borohydride; water; sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 2h;

With salicylic acid; at 60 ℃; for 2h;

Reference yield:

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathiolane-2-carboxylate (147027-10-9,147126-73-6,147126-74-7,147126-80-5) + salicylic acid (69-72-7,25496-36-0,8052-31-1) → lamivudine salicyclic acid salt (173522-96-8)

Guidance literature:

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathiolane-2-carboxylate; With sodium tetrahydroborate; dipotassium hydrogenphosphate; In methanol; water; at 18 - 22 ℃; for 6h;

salicylic acid; In water; at 78 - 82 ℃;

Reference yield:

lamivudine (134678-17-4) + salicylic acid (69-72-7,25496-36-0,8052-31-1) → lamivudine salicyclic acid salt (173522-96-8)

Guidance literature:

lamivudine; salicylic acid; In water; at 10 - 82 ℃; for 8h;

In water;

upstream raw materials:

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathiolane-2-carboxylate

salicylic acid

lamivudine

Downstream raw materials:

lamivudine

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF SUBSTITUTED 1,3-OXATHIOLANES". Page/Page column 7. . Retrieved 2010/12/29.
• 2、 -. "PROCESS AND INTERMEDIATES FOR THE PREPARATION OF SUBSTITUTED 1, 3-OXATHIOLANES, ESPECIALLY LAMIVUDINE". Page/Page column 22-23. . Retrieved 2009/07/03.