N4-Benzoyl-5-fluorocytosine

Base Information

• Chemical Name: N4-Benzoyl-5-fluorocytosine
• CAS No.: 10357-07-0
• Molecular Formula: C11H8 F N3 O2
• Molecular Weight: 233.202
• Hs Code.: 2933599090
• Mol file: 10357-07-0.mol

Synonyms:Benzamide,N-(5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinyl)- (9CI); Cytosine,N-benzoyl-5-fluoro- (7CI); N4-Benzoyl-5-fluorocytosine; NSC 527094

Chemical Property of N4-Benzoyl-5-fluorocytosine

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 74.85000
• Density: 1.41g/cm³
• LogP: 1.23430
• Storage Temp.: 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-(5-Fluoro-2-oxo-2,3-dihydropyrimidin-4-yl)benzamide 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N4-Benzoyl-5-fluorocytosine

There total 2 articles about N4-Benzoyl-5-fluorocytosine 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: 99.0%

Flucytosine (2022-85-7) + benzoyl chloride (98-88-4) → N-benzoyl-5-fluorocytosine (10357-07-0)

Guidance literature:

With pyridine; at 0 - 20 ℃; for 16h; Inert atmosphere;

DOI:10.1021/acs.orglett.5b00982

Reference yield: 70.0%

Flucytosine (2022-85-7) + benzoic acid anhydride (93-97-0) → N-benzoyl-5-fluorocytosine (10357-07-0)

Guidance literature:

With dmap; In acetonitrile; for 24h; Inert atmosphere; Reflux;

DOI:10.1039/d1ob00493j

Reference yield: 90.0%

N-benzoyl-5-fluorocytosine (10357-07-0) + (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate (147027-09-6,147126-67-8) → (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-[5-fluoro-2-oxo-4-(phenylcarboxamido)-1,2-dihydro-1-pyrimidinyl]-1,3-oxathiolane-2-carboxylate

Guidance literature:

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate; With iodine; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;

N-benzoyl-5-fluorocytosine; With N,O-bis-(trimethylsilyl)-acetamide; In dichloromethane; at 0 - 20 ℃; for 1h; Reagent/catalyst; stereoselective reaction; Inert atmosphere;

DOI:10.1021/acs.orglett.5b00982

upstream raw materials:

Flucytosine

benzoyl chloride

benzoic acid anhydride

Downstream raw materials:

N-(5-Fluoro-2-trimethylsilanyloxy-pyrimidin-4-yl)-benzamide

5-fluoro-1-<5-O-(tert-butyldimethylsilyl)-2,3-dideoxy-2-fluoro-α-L-glycero-pent-2-enofuranosyl>-N⁴-benzoylcytosine

5-fluoro-1-<5-O-(tert-butyldimethylsilyl)-2,3-dideoxy-2-fluoro-β-L-glycero-pent-2-enofuranosyl>-N⁴-benzoylcytosine

(-)-N⁴-benzoyl-1-[(1S,2S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-4-thio-β-L-ribofuranosyl]-5-fluorocytosine

Refernces

• 1、 Caso, Maria Federica,Dalonzo, Daniele,Derrico, Stefano,Palumbo, Giovanni,Guaragna, Annalisa. "Highly stereoselective synthesis of lamivudine (3TC) and emtricitabine (FTC) by a novel N -glycosidation procedure". supporting information. p. 2626 - 2629. Retrieved 2015/06/16.