P-[[(1S)-2-[4-(Benzoylamino)-2-oxo-1(2H)-pyrimidinyl]-1-(hydroxymethyl)ethoxy]methyl]phosphonic acid diethyl ester CAS#: 132336-36-8; 凯望编码 (ChemWhat Code): 500539

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

英文名P-[[(1S)-2-[4-(Benzoylamino)-2-oxo-1(2H)-pyrimidinyl]-1-(hydroxymethyl)ethoxy]methyl]phosphonic acid diethyl ester
IUPAC NameN-[1-[2-(diethoxyphosphorylmethoxy)-3-hydroxypropyl]-2-oxopyrimidin-4-yl]benzamide
分子结构P-1S-2-4-Benzoylamino-2-oxo-12H-pyrimidinyl-1-hydroxymethylethoxymethylphosphonic-acid-diethyl-ester-CAS-132336-36-8
CAS编号 132336-36-8
别名132336-36-8
Diethyl (((1-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-3-hydroxypropan-2-yl)oxy)methyl)phosphonate
N-[1-[2-(diethoxyphosphorylmethoxy)-3-hydroxypropyl]-2-oxopyrimidin-4-yl]benzamide
N-Benzoyl rac-Cidofovir Diethyl Phosphonate
P-[[(1S)-2-[4-(BenzoylaMino)-2-oxo-1(2H)-pyriMidinyl]-1-(hydroxyMethyl)ethoxy]Methyl]phosphonic acid diethyl ester
Diethyl ({[1-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-3-hydroxypropan-2-yl]oxy}methyl)phosphonate
DTXSID10563919
BCP24064
AKOS016006433
分子式C19H26N3O7P 
分子量439.4
InChIInChI=1S/C19H26N3O7P/c1-3-28-30(26,29-4-2)14-27-16(13-23)12-22-11-10-17(21-19(22)25)20-18(24)15-8-6-5-7-9-15/h5-11,16,23H,3-4,12-14H2,1-2H3,(H,20,21,24,25) 
InChI KeyWYJNVSZEUBNGND-UHFFFAOYSA-N
Isomeric SMILESCCOP(=O)(COC(CN1C=CC(=NC1=O)NC(=O)C2=CC=CC=C2)CO)OCC
Patent Information
Patent IDTitlePublication Date
CN111018912Synthesis and purification method of antiviral drug key intermediate2020

Physical Data

AppearancePowder

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)
Chemical shifts1Hchloroform-d1
Chemical shifts13Cchloroform-d1
Chemical shifts31Pchloroform-d1
Chemical shifts, Spectrum1Hchloroform-d1
Chemical shifts, Spectrum13Cchloroform-d1
Chemical shifts, Spectrum31Pchloroform-d1

Route of Synthesis (ROS)

Route of Synthesis (ROS) of P-[[(1S)-2-[4-(Benzoylamino)-2-oxo-1(2H)-pyrimidinyl]-1-(hydroxymethyl)ethoxy]methyl]phosphonic acid diethyl ester CAS 132336-36-8
Route of Synthesis (ROS) of P-[[(1S)-2-[4-(Benzoylamino)-2-oxo-1(2H)-pyrimidinyl]-1-(hydroxymethyl)ethoxy]methyl]phosphonic acid diethyl ester CAS 132336-36-8
ConditionsYield
With hydrogen bromide In dichloromethane at 20℃;

Experimental Procedure
2; 4 Example 2 <br/>Synthesis of Cidofovir key intermediate (s) -N4-benzoyl-N1-[(2-phosphatemethoxy-3-hydroxy) propyl] cytosine
The (s) -N4-benzoyl-N1-[(2-diethyl phosphatemethoxy-3-triphenylmethoxy) propyl] cytosine (4.00 g, 5.87 mmol) obtained in Example 1 was dissolved In 40ml of dichloromethane,Add 16ml of 40% hydrobromic acid,After reacting at room temperature overnight, TLC monitors the disappearance of the starting point,Stop the reaction, separate the liquid, adjust the pH of the aqueous phase to neutral to precipitate a white solid,Filtration can obtain 1.88g of crude target product (yield 83.6%).		92%
With hydrogenchloride In dichloromethane at 0 – 5℃; for 0.166667h; Yield given

Safety and Hazards

GHS Hazard StatementsNot Classified

Other Data

TransportationStore at 2~8° for long time.
HS Code
StorageStore at 2~8° for long time.
Shelf Life1 year
Market Price
Druglikeness
Lipinski rules component
分子量439.405
logP0.116
HBA10
HBD2
Matching Lipinski Rules4
Veber rules component
Polar Surface Area (PSA)136.57
Rotatable Bond (RotB)13
Matching Veber Rules1
Use Pattern
P-[[(1S)-2-[4-(Benzoylamino)-2-oxo-1(2H)-pyrimidinyl]-1-(hydroxymethyl)ethoxy]methyl]phosphonic acid diethyl ester is an important intermediate in the synthesis of Cidofovir. Cidofovir is an antiviral medication used primarily for the treatment of cytomegalovirus (CMV) infections, particularly in patients with weakened immune systems, such as those with AIDS.

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