(S)-isopropyl 2-(((S)-(perfluorophenoxy)(phenoxy)phosphoryl)amino)propanoate

Base Information

• Chemical Name: (S)-isopropyl 2-(((S)-(perfluorophenoxy)(phenoxy)phosphoryl)amino)propanoate
• CAS No.: 1334513-02-8
• Molecular Formula: C18H17F5NO5P
• Molecular Weight: 453.302
• Hs Code.: 2931599090
• European Community (EC) Number: 695-076-0
• DSSTox Substance ID: DTXSID301019342
• Mol file: 1334513-02-8.mol

Synonyms:1334513-02-8;(S)-isopropyl 2-(((S)-(perfluorophenoxy)(phenoxy)phosphoryl)amino)propanoate;propan-2-yl (2S)-2-{[(S)-pentafluorophenoxy(phenoxy)phosphoryl]amino}propanoate;N-[(S)-(2,3,4,5,6-Pentafluorophenoxy)Phenoxyphosphinyl]-L-Alanine 1-Methylethyl Ester;MFCD22665799;SCHEMBL2510990;Propan-2-yl N-[(S)-(pentafluorophenoxy)(phenoxy)-phosphoryl]-L-alanine;AMY4182;MIILDBHEJQLACD-ZJPIPACBSA-N;N-((S)-(2,3,4,5,6-pentafluorophenoxy)phenoxyphosphinyl)-l-alanine 1-methylethyl ester;DTXSID301019342;CS-B0630;isopropyl ((S)-(perfluorophenoxy)(phenoxy)phosphoryl)-L-alaninate;AKOS025286071;propan-2-yl (2S)-2-{[(S)-;PB11574;PB35955;HY-59121;PD196034;pentafluorophenoxy(phenoxy)phosphoryl]amino}propanoate;propan-2-yl (2S)-2-[[(2,3,4,5,6-pentafluorophenoxy)-;Isopropyl N-[(S)-(pentafluorophenoxy)(phenoxy)phosphoryl]-L-alaninate;(S)-isopropyl 2-(((S)-(perfluorophenoxy)(phenoxy)phosphoryl)-amino)propanoate;L-Alanine, N-[(S)-(2,3,4,5,6-pentafluorophenoxy)-phenoxyphosphinyl]-, 1-methylethyl ester;N-[(S)-(2,3,4,5,6-pentafluorophenoxy)phenoxyphosphinyl]-L-alanine1-Methylethylester

Chemical Property of (S)-isopropyl 2-(((S)-(perfluorophenoxy)(phenoxy)phosphoryl)amino)propanoate

Chemical Property:

• Vapor Pressure: 0Pa at 25℃
• Boiling Point: 442.6±55.0 °C(Predicted)
• PKA: -3.81±0.70(Predicted)
• PSA: 83.67000
• Density: 1.405
• LogP: 5.26860
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 9
• Exact Mass: 453.07645045
• Heavy Atom Count: 30
• Complexity: 608

Purity/Quality:

≥98.0% ^*data from raw suppliers

2’-Defluro-2’-hydroxy2’-epi-Sofosbuvir ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)OC(=O)C(C)NP(=O)(OC1=CC=CC=C1)OC2=C(C(=C(C(=C2F)F)F)F)F
• Isomeric SMILES: C[C@@H](C(=O)OC(C)C)N[P@](=O)(OC1=CC=CC=C1)OC2=C(C(=C(C(=C2F)F)F)F)F
• Uses: N-[(S)-(2,3,4,5,6-Pentafluorophenoxy)phenoxyphosphinyl]-L-alanine 1-Methylethyl Ester is a reactant in the synthesis of phosphoramidate imidazo[2,1-f][1,2,4]triazine-4-amine adenosine prodrugs that can increase anti-HCV activity.

Technology Process of (S)-isopropyl 2-(((S)-(perfluorophenoxy)(phenoxy)phosphoryl)amino)propanoate

There total 17 articles about (S)-isopropyl 2-(((S)-(perfluorophenoxy)(phenoxy)phosphoryl)amino)propanoate 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: 88.0%

2,3,4,5,6-pentafluorophenol (771-61-9) + O-phenyl phosphorodichloridate (770-12-7) + alanine isopropyl ester hydrochloride (39613-92-8,62062-56-0,62062-65-1) → (S)-2-[(S)-((2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester (1334513-02-8,1627824-09-2)

Guidance literature:

2,3,4,5,6-pentafluorophenol; O-phenyl phosphorodichloridate; With triethylamine; In chloroform; at 0 ℃; under 11251.1 Torr;

alanine isopropyl ester hydrochloride; In chloroform; Temperature;

Reference yield: 66.81%

phenyl(isopropoxy-L-alaninyl) phosphorochloridate (261909-49-3) + sodium pentafluorophenolate (2263-53-8) → (S)-2-[(S)-((2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester (1334513-02-8,1627824-09-2)

Guidance literature:

phenyl(isopropoxy-L-alaninyl) phosphorochloridate; sodium pentafluorophenolate; In tetrahydrofuran; at -10 ℃;

With triethylamine; In n-heptane; tert-butyl methyl ether; pH=8;

Reference yield: 56.0%

(S)-2-[(2,3,4,5,6-pentafluorophenoxy)phenoxyphosphorylamino]propionic acid isopropyl ester (1256490-52-4,1627824-09-2) → (S)-2-[(S)-((2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester (1334513-02-8,1627824-09-2)

Guidance literature:

With triethylamine; In cyclohexane; at 30 - 80 ℃; for 6h;

upstream raw materials:

2,3,4,5,6-pentafluorophenyl dichlorophosphate

alanine isopropyl ester hydrochloride

2,3,4,5,6-pentafluorophenol

O-phenyl phosphorodichloridate

Downstream raw materials:

sofosbuvir

(S)-isopropyl 2-(((S)-(((2R,3R,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

(S)-isopropyl 2-(((S)-(((3aR,4R,6R,6aR)-6-(6-amino-0H-purin-9-yl)-2,2-dimethyltetrahydrofuro-[3,4-d]dioxol-4-yl)methoxy)(phenoxy)phosphoryl)amino)propionoate

(S)-isopropyl 2-(((S)-(((3aR,4R,6R,6aR)-6-(2-amino-6-oxo-1H-purin-9(6H)-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]-dioxol-4-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Refernces

• 1、 -. "Nucleotide derivative and pharmaceutical composition and application thereof". . . Retrieved 2021/08/25.
• 2、 -. "Method for preparing sofosbuvir intermediate by using microfluid reaction device". Paragraph 0046-0054. . Retrieved 2020/04/17.