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CAS No.: | 1334513-02-8 |
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Name: | N-[(S)-(2,3,4,5,6-pentafluorophenoxy)phenoxyphosphinyl]-L-alanine 1-Methylethyl ester |
Molecular Structure: | |
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Formula: | C18H17F5NO5P |
Molecular Weight: | 453.302 |
Synonyms: | L-Alanine, N-[(2,3,4,5,6-pentafluorophenoxy)phenoxyphosphinyl]-, 1-methylethyl ester; N-[(S)-(2,3,4,5,6-Pentafluorophenoxy)Phenoxyphosphinyl]-L-Alanine 1-Methylethyl Ester; N-[(S)-(2,3,4,5,6-Penta fluorophenoxy)phenoxy phosphinyl]-L-alanine 1-methylethyl ester; Sofosbuvir Side Chain; N-[(S)-(2,3,4,5,6-Pentafluorophenoxy)-phenoxyphosphinyl]-L-alanine 1-methylethyl ester; N-[(S)-(2,3,4,5,6-pentafluorophenoxy)phenoxyphosphinyl]-L-alanine1-Methylethyl ester; N-((S)-(2,3,4,5,6-Pentafluoro Phenoxy) Phenoxy Phosphinyl)-L--Alanine-1-Methyl Ethyl Ester; n-((s)-(2,3,4,5,6-pentafluorophenoxy)phenoxyphosphinyl)-l-alanine1-methylethylester; (2s)-isopropyl-2-((perfluorophenoxyl)(phenoxy)phosphorylamino)Propanoate |
EINECS: | 695-076-0 |
Density: | 1.405 |
Boiling Point: | 442.6±55.0 °C(Predicted) |
PSA: | 83.67000 |
LogP: | 5.26860 |
2,3,4,5,6-pentafluorophenol
O-phenyl phosphorodichloridate
alanine isopropyl ester hydrochloride
(S)-2-[((S)-(2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester
Conditions | Yield |
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Stage #1: 2,3,4,5,6-pentafluorophenol; O-phenyl phosphorodichloridate With triethylamine In chloroform at 0℃; under 11251.1 Torr; Stage #2: alanine isopropyl ester hydrochloride In chloroform Temperature; | 88% |
Stage #1: alanine isopropyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane at -68℃; for 0.5h; Stage #2: O-phenyl phosphorodichloridate In dichloromethane at -10℃; for 0.5h; Stage #3: 2,3,4,5,6-pentafluorophenol With N-ethyl-N,N-diisopropylamine In dichloromethane | 78% |
Stage #1: O-phenyl phosphorodichloridate; alanine isopropyl ester hydrochloride With triethylamine In dichloromethane at -78 - 20℃; for 2h; Stage #2: 2,3,4,5,6-pentafluorophenol With triethylamine In dichloromethane at -78 - 20℃; for 3h; | 61.6% |
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
sodium pentafluorophenolate
(S)-2-[((S)-(2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester
Conditions | Yield |
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Stage #1: phenyl(isopropoxy-L-alaninyl) phosphorochloridate; sodium pentafluorophenolate In tetrahydrofuran at -10℃; Stage #2: With triethylamine In n-heptane; tert-butyl methyl ether pH=8; | 66.81% |
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
2,3,4,5,6-pentafluorophenol
(S)-2-[((S)-(2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester
Conditions | Yield |
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With triethylamine In dichloromethane at 0℃; for 4h; | 45.1% |
With triethylamine In dichloromethane at 0℃; for 4h; Inert atmosphere; | 45.1% |
2,3,4,5,6-pentafluorophenyl dichlorophosphate
alanine isopropyl ester hydrochloride
A
(S)-2-[((S)-(2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester
B
(S)-2-[(S)-(2,3,4,5,6-pentafluoro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester
Conditions | Yield |
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Stage #1: 2,3,4,5,6-pentafluorophenyl dichlorophosphate With triethylamine; phenol In dichloromethane at 20℃; for 0.5h; Stage #2: alanine isopropyl ester hydrochloride With triethylamine In dichloromethane at 0℃; for 1h; |
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
2,3,4,5,6-pentafluorophenol
A
(S)-2-[((S)-(2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester
B
(S)-2-[(S)-(2,3,4,5,6-pentafluoro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester
Conditions | Yield |
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With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere; | |
With triethylamine In dichloromethane at -10 - 0℃; for 1.5h; | A n/a B n/a |
With triethylamine In dichloromethane at -15 - 5℃; for 1h; Inert atmosphere; | A n/a B n/a |
alanine isopropyl ester hydrochloride
A
(S)-2-[((S)-(2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester
B
(S)-2-[(S)-(2,3,4,5,6-pentafluoro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester
Conditions | Yield |
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Multi-step reaction with 2 steps 1: dichloromethane / 0.5 h / -10 °C / Inert atmosphere 2: triethylamine / dichloromethane / 1.5 h / -10 - 0 °C View Scheme | |
Multi-step reaction with 2 steps 1: triethylamine / tert-butyl methyl ether / 2 h / -65 - -50 °C / Inert atmosphere; Cooling with acetone-dry ice 2: triethylamine / dichloromethane / 1 h / -15 - 5 °C / Inert atmosphere View Scheme |
O-phenyl phosphorodichloridate
A
(S)-2-[((S)-(2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester
B
(S)-2-[(S)-(2,3,4,5,6-pentafluoro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester
Conditions | Yield |
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Multi-step reaction with 2 steps 1: dichloromethane / 0.5 h / -10 °C / Inert atmosphere 2: triethylamine / dichloromethane / 1.5 h / -10 - 0 °C View Scheme |
2,3,4,5,6-pentafluorophenol
O-phenyl phosphorodichloridate
alanine isopropyl ester hydrochloride
A
(S)-2-[((S)-(2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester
Conditions | Yield |
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Stage #1: alanine isopropyl ester hydrochloride With triethylamine In dichloromethane at -70℃; for 0.75h; Stage #2: O-phenyl phosphorodichloridate In dichloromethane at -70 - 0℃; for 8h; Stage #3: 2,3,4,5,6-pentafluorophenol With triethylamine In dichloromethane at 0 - 20℃; |
O-phenyl phosphorodichloridate
(S)-2-[((S)-(2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester
Conditions | Yield |
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Multi-step reaction with 2 steps 1.1: triethylamine / ethyl acetate / 1 h / -10 °C / Enzymatic reaction 1.2: 2.5 h / -5 - 25 °C 2.1: triethylamine / ethyl acetate; n-heptane / 4 - 8 h / Resolution of racemate View Scheme | |
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 1.5 h / -60 - 25 °C / Inert atmosphere 2.1: tetrahydrofuran / -10 °C 2.2: pH 8 View Scheme | |
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 20 h / -70 - 20 °C 2: triethylamine / dichloromethane / 20 h / -5 - 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 1 h / -78 - 20 °C 2: triethylamine / dichloromethane / 4 h / 0 °C View Scheme |
isopropyl L-alanine
(S)-2-[((S)-(2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester
Conditions | Yield |
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Multi-step reaction with 2 steps 1.1: triethylamine / ethyl acetate / 1 h / -10 °C / Enzymatic reaction 1.2: 2.5 h / -5 - 25 °C 2.1: triethylamine / ethyl acetate; n-heptane / 4 - 8 h / Resolution of racemate View Scheme |