Nelfinavir supplier | CasNO.159989-64-7

Name
Nelfinavir
EINECS 1533716-785-6
CAS No. 159989-64-7
Article Data12
CAS DataBase
Density 1.226 g/cm³
Solubility 7g/L(temperature not stated)
Melting Point 185-186 °C
Formula C₃₂H₄₅N₃O₄S
Boiling Point 786.839 °C at 760 mmHg
Molecular Weight 567.793
Flash Point 429.665 °C
Transport Information
Appearance white to off-white crystalline powder
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 3-Isoquinolinecarboxamide,N-(1,1-dimethylethyl)decahydro-2-[2-hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-(phenylthio)butyl]-,[3S-[2(2S*,3S*),3a,4ab,8ab]]-;AG 1341;(3S,4aS,8aS)-2-[(2R,3R)-2-Hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-(phenylsulfanyl)butyl]-N-(2-methyl-2-propanyl)decahydro-3-isoquinolinecarboxamide;
PSA 189.95000
LogP 6.05210

Synthetic route

: 108-98-5
thiophenol

: 188936-07-4
(3S,4aS,8aS)-N-tert-butyl-2-((R)-2-hydroxy-2-((S)-2-(3-hydroxy-2-methylphenyl)-4,5-dihydrooxazol-4-yl)ethyl)-decahydroisoquinoline-3-carboxamide

A: 159989-64-7
nelfinavir

B: 1025935-06-1
(3S,4aS,8aS)-2-[(2S,3S)-3-Hydroxy-2-(3-hydroxy-2-methyl-benzoylamino)-4-phenylsulfanyl-butyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide

Conditions

Conditions	Yield
With potassium hydrogencarbonate In various solvent(s) at 115℃; for 4h;	A 84% B 8 % Chromat.
With triethylamine In N,N-dimethyl-formamide at 80℃; for 10h; Product distribution; other base, other temperature, other solvents;	A 84 % Chromat. B 16 % Chromat.
In ethylene glycol at 120℃; for 20h;	A 18 % Chromat. B 82 % Chromat.

...Expand

: 108-98-5
thiophenol

: 188936-07-4
(3S,4aS,8aS)-N-tert-butyl-2-((R)-2-hydroxy-2-((S)-2-(3-hydroxy-2-methylphenyl)-4,5-dihydrooxazol-4-yl)ethyl)-decahydroisoquinoline-3-carboxamide

: 159989-64-7
nelfinavir

Conditions

Conditions	Yield
	82%
With potassium hydrogencarbonate at 140℃; for 5h; Sealed tube;	78%
With potassium hydrogencarbonate In various solvent(s) Substitution;	72%
With triethylamine In water; N,N-dimethyl-formamide; toluene; butanone	65%

: 167678-46-8
3-acetoxy-2-methylbenzoyl chloride

: (2R,3R)-4-((3S,4aS,8aS)-3-(tertbutylcarbamoyl)octahydroisoquinolin-2(1H)-yl)-3-hydroxy-1-(phenylthio)butan-2-aminium benzoate

: 159989-64-7
nelfinavir

Conditions

Conditions	Yield
Stage #1: 3-acetoxy-2-methylbenzoyl chloride; (2R,3R)-4-((3S,4aS,8aS)-3-(tertbutylcarbamoyl)octahydroisoquinolin-2(1H)-yl)-3-hydroxy-1-(phenylthio)butan-2-aminium benzoate In ethanol Stage #2: With sodium hydroxide	79%

active charcoal: active charcoal

: 108-98-5
thiophenol

: 78-93-3
butanone

: 188936-07-4
(3S,4aS,8aS)-N-tert-butyl-2-((R)-2-hydroxy-2-((S)-2-(3-hydroxy-2-methylphenyl)-4,5-dihydrooxazol-4-yl)ethyl)-decahydroisoquinoline-3-carboxamide

: 159989-64-7
nelfinavir

Conditions

Conditions	Yield
In pyridine	69%

...Expand

: 128019-40-9, 149510-73-6, 136465-81-1
(3S,4aS,8aS)-N-tert-butyl-decahydroisoquinoline-3-carboxamide

: 767341-27-5
Acetic acid 3-((1R,2S)-2,3-dihydroxy-1-phenylsulfanylmethyl-propylcarbamoyl)-2-methyl-phenyl ester

: 159989-64-7
nelfinavir

Conditions

Conditions	Yield
Stage #1: Acetic acid 3-((1R,2S)-2,3-dihydroxy-1-phenylsulfanylmethyl-propylcarbamoyl)-2-methyl-phenyl ester With triethylamine; p-toluenesulfonyl chloride Stage #2: (3S,4aS,8aS)-N-tert-butyl-decahydroisoquinoline-3-carboxamide	59%

: (3S,4AS,8AS)-2-[(2R,3R)-3-(3-acetoxy-2-methylbenzoylamino)-2-hydroxy-4-phenylthiobutyl]decahydroisoquinoline-3-carboxylic acid t-butylamide

: 159989-64-7
nelfinavir

Conditions

Conditions	Yield
With ammonia; water In methanol at 20℃; for 1.5h;	54%
With ammonia; water In methanol at 20℃; for 3h; Inert atmosphere;	884 mg
Stage #1: (3S,4AS,8AS)-2-[(2R,3R)-3-(3-acetoxy-2-methylbenzoylamino)-2-hydroxy-4-phenylthiobutyl]decahydroisoquinoline-3-carboxylic acid t-butylamide With sodium hydroxide; water; benzyl alcohol at 20 - 82℃; for 0.583333h; pH=14; Stage #2: With water; acetic acid In benzyl alcohol at 53℃; pH=7 - 7.5; Product distribution / selectivity;

: (2R,3S)-3-(3-acetoxy-2-methylbenzamido)-1-((3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl)-4-hydroxybutan-2-yl-4-methoxybenzoate

: 108-98-5
thiophenol

A: 159989-64-7
nelfinavir

B: 1025935-06-1
(3S,4aS,8aS)-2-[(2S,3S)-3-Hydroxy-2-(3-hydroxy-2-methyl-benzoylamino)-4-phenylsulfanyl-butyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide

Conditions

Conditions	Yield
Stage #1: (2R,3S)-3-(3-acetoxy-2-methylbenzamido)-1-((3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl)-4-hydroxybutan-2-yl-4-methoxybenzoate With methanesulfonyl chloride; triethylamine In N,N-dimethyl-formamide at 20℃; Stage #2: thiophenol at 120℃; Stage #3: With potassium carbonate In methanol at 40℃;	A 31% B 41%

...Expand

: 168899-58-9
3-acetoxy-2-methylbenzoic acid

: 159989-64-7
nelfinavir

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 72 percent / EDCI; HOBt 2: 100 percent / HCl / methanol / 3 h / 40 °C 3: 59 percent / TsCl; Et3N View Scheme

: 1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-phenylsulfanyl-ethylamine

: 159989-64-7
nelfinavir

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 72 percent / EDCI; HOBt 2: 100 percent / HCl / methanol / 3 h / 40 °C 3: 59 percent / TsCl; Et3N View Scheme

: 2-Benzenesulfinyl-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethylamine

: 159989-64-7
nelfinavir

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 71 percent / BF3*Et2O; NaI 2: 72 percent / EDCI; HOBt 3: 100 percent / HCl / methanol / 3 h / 40 °C 4: 59 percent / TsCl; Et3N View Scheme

: 767341-31-1
Acetic acid 3-[(R)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-phenylsulfanyl-ethylcarbamoyl]-2-methyl-phenyl ester

: 159989-64-7
nelfinavir

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 100 percent / HCl / methanol / 3 h / 40 °C 2: 59 percent / TsCl; Et3N View Scheme

: 128019-40-9, 149510-73-6, 136465-81-1
(3S,4aS,8aS)-N-tert-butyl-decahydroisoquinoline-3-carboxamide

: 159989-64-7
nelfinavir

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: K2CO3 / propan-2-ol / Heating View Scheme
Multi-step reaction with 2 steps 1: K2CO3 / methanol; H2O / 5 h / 50 °C 2: 72 percent / KHCO3 / various solvent(s) View Scheme
Multi-step reaction with 7 steps 1.1: sodium carbonate / N,N-dimethyl-formamide / 30 h / 120 °C 2.1: hydrogenchloride / tetrahydrofuran; water / 3.5 h / 20 °C 3.1: triethylamine / dichloromethane / 0.5 h / 0 - 20 °C 4.1: hydrogenchloride; ozone; oxygen / dichloromethane; ethyl acetate / 0.58 h / -78 °C 4.2: 3 h / -78 - 0 °C 5.1: triethylamine; methanesulfonyl chloride / N,N-dimethyl-formamide / 0.33 h / 20 °C 5.2: 3 h / 50 °C 6.1: potassium carbonate / methanol / 2 h / 100 °C / Sealed tube 7.1: potassium hydrogencarbonate / 5 h / 140 °C / Sealed tube View Scheme

: 201402-95-1
Acetic acid 3-{(S)-4-[(S)-1-hydroxy-2-(toluene-4-sulfonyloxy)-ethyl]-4,5-dihydro-oxazol-2-yl}-2-methyl-phenyl ester

: 159989-64-7
nelfinavir

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: K2CO3 / propan-2-ol / Heating View Scheme

: 167678-46-8
3-acetoxy-2-methylbenzoyl chloride

: 159989-64-7
nelfinavir

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: Et3N / ethyl acetate / 1.75 h / 20 °C 1.2: H2SO4 (98 percent) / ethyl acetate / 17 h / 20 °C 2.1: K2CO3 / methanol; H2O / 5 h / 50 °C 3.1: 72 percent / KHCO3 / various solvent(s) View Scheme
Multi-step reaction with 5 steps 1: NaHCO3 / CH2Cl2; H2O 2: Et3N / CH2Cl2 3: 1.) BF3*Et2O / 1.) CH2Cl2 4: K2CO3 / methanol; H2O 5: 18 percent Chromat. / ethane-1,2-diol / 20 h / 120 °C View Scheme

: 188936-06-3
(2R)-1-acetoxy-2-((4S)-2-(3-acetoxy-2-methylphenyl)-4,5-dihydrooxazol-4-yl)-2-methanesulfonyloxyethane

: 159989-64-7
nelfinavir

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: K2CO3 / methanol; H2O / 5 h / 50 °C 2: 72 percent / KHCO3 / various solvent(s) View Scheme
Multi-step reaction with 2 steps 1: K2CO3 / methanol; H2O 2: 18 percent Chromat. / ethane-1,2-diol / 20 h / 120 °C View Scheme

: 188936-02-9
Acetic acid 3-((5S,6R)-6-hydroxy-2,2-dimethyl-[1,3]dioxepan-5-ylcarbamoyl)-2-methyl-phenyl ester

: 159989-64-7
nelfinavir

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: Et3N / CH2Cl2 2: 1.) BF3*Et2O / 1.) CH2Cl2 3: K2CO3 / methanol; H2O 4: 18 percent Chromat. / ethane-1,2-diol / 20 h / 120 °C View Scheme

: 188936-03-0
Acetic acid 3-((5S,6R)-6-methanesulfonyloxy-2,2-dimethyl-[1,3]dioxepan-5-ylcarbamoyl)-2-methyl-phenyl ester

: 159989-64-7
nelfinavir

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) BF3*Et2O / 1.) CH2Cl2 2: K2CO3 / methanol; H2O 3: 18 percent Chromat. / ethane-1,2-diol / 20 h / 120 °C View Scheme

: 167678-46-8
3-acetoxy-2-methylbenzoyl chloride

: 159878-04-3
(3S,4aS,8aS)-N-tert-butyl-2-[(2R,3R)-3-benzyloxycarbonylamino-2-hydroxy-4-(phenylthio)butyl]decahydroisoquinoline-3-carboxamide

: 159989-64-7
nelfinavir

Conditions

Conditions	Yield
Stage #1: (3S,4aS,8aS)-N-tert-butyl-2-[(2R,3R)-3-benzyloxycarbonylamino-2-hydroxy-4-(phenylthio)butyl]decahydroisoquinoline-3-carboxamide Alkaline aqueous solution; Heating / reflux; Stage #2: 3-acetoxy-2-methylbenzoyl chloride In water Alkaline aqueous solution;

: 603-80-5
3-hydroxy 2-methylbenzoic acid

: (2R,3R)-4-((3S,4aS,8aS)-3-(tertbutylcarbamoyl)octahydroisoquinolin-2(1H)-yl)-3-hydroxy-1-(phenylthio)butan-2-aminium benzoate

: 159989-64-7
nelfinavir

Conditions

Conditions	Yield
Stage #1: 3-hydroxy 2-methylbenzoic acid; (2R,3R)-4-((3S,4aS,8aS)-3-(tertbutylcarbamoyl)octahydroisoquinolin-2(1H)-yl)-3-hydroxy-1-(phenylthio)butan-2-aminium benzoate In methanol Stage #2: With sodium hydroxide

: (3S,4aS,8aS)-N-tert-butyl-2-(((4S,5R)-2-(4-methoxyphenyl)-4-vinyl-4,5-dihydrooxazol-5-yl)methyl)decahydroisoquinoline-3-carboxamide

: 159989-64-7
nelfinavir

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: hydrogenchloride / tetrahydrofuran; water / 3.5 h / 20 °C 2.1: triethylamine / dichloromethane / 0.5 h / 0 - 20 °C 3.1: hydrogenchloride; ozone; oxygen / dichloromethane; ethyl acetate / 0.58 h / -78 °C 3.2: 3 h / -78 - 0 °C 4.1: triethylamine; methanesulfonyl chloride / N,N-dimethyl-formamide / 0.33 h / 20 °C 4.2: 3 h / 50 °C 5.1: potassium carbonate / methanol / 2 h / 100 °C / Sealed tube 6.1: potassium hydrogencarbonate / 5 h / 140 °C / Sealed tube View Scheme

Yield

Multi-step reaction with 6 steps
1.1: hydrogenchloride / tetrahydrofuran; water / 3.5 h / 20 °C
2.1: triethylamine / dichloromethane / 0.5 h / 0 - 20 °C
3.1: hydrogenchloride; ozone; oxygen / dichloromethane; ethyl acetate / 0.58 h / -78 °C
3.2: 3 h / -78 - 0 °C
4.1: triethylamine; methanesulfonyl chloride / N,N-dimethyl-formamide / 0.33 h / 20 °C
4.2: 3 h / 50 °C
5.1: potassium carbonate / methanol / 2 h / 100 °C / Sealed tube
6.1: potassium hydrogencarbonate / 5 h / 140 °C / Sealed tube
View Scheme

: (3S,4aS,8aS)-N-tert-butyl-2-(((4S,5R)-2-(4-methoxyphenyl)-4-vinyl-4,5-dihydrooxazol-5-yl)methyl)decahydroisoquinoline-3-carboxamide

A: 159989-64-7
nelfinavir

B: 1025935-06-1
(3S,4aS,8aS)-2-[(2S,3S)-3-Hydroxy-2-(3-hydroxy-2-methyl-benzoylamino)-4-phenylsulfanyl-butyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: hydrogenchloride / tetrahydrofuran; water / 3.5 h / 20 °C 2.1: triethylamine / dichloromethane / 0.5 h / 0 - 20 °C 3.1: hydrogenchloride; ozone; oxygen / dichloromethane; ethyl acetate / 0.58 h / -78 °C 3.2: 3 h / -78 - 0 °C 4.1: triethylamine; methanesulfonyl chloride / N,N-dimethyl-formamide / 20 °C 4.2: 120 °C 4.3: 40 °C View Scheme

: 128019-40-9, 149510-73-6, 136465-81-1
(3S,4aS,8aS)-N-tert-butyl-decahydroisoquinoline-3-carboxamide

A: 159989-64-7
nelfinavir

B: 1025935-06-1
(3S,4aS,8aS)-2-[(2S,3S)-3-Hydroxy-2-(3-hydroxy-2-methyl-benzoylamino)-4-phenylsulfanyl-butyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: sodium carbonate / N,N-dimethyl-formamide / 30 h / 120 °C 2.1: hydrogenchloride / tetrahydrofuran; water / 3.5 h / 20 °C 3.1: triethylamine / dichloromethane / 0.5 h / 0 - 20 °C 4.1: hydrogenchloride; ozone; oxygen / dichloromethane; ethyl acetate / 0.58 h / -78 °C 4.2: 3 h / -78 - 0 °C 5.1: triethylamine; methanesulfonyl chloride / N,N-dimethyl-formamide / 20 °C 5.2: 120 °C 5.3: 40 °C View Scheme

Yield

Multi-step reaction with 5 steps
1.1: sodium carbonate / N,N-dimethyl-formamide / 30 h / 120 °C
2.1: hydrogenchloride / tetrahydrofuran; water / 3.5 h / 20 °C
3.1: triethylamine / dichloromethane / 0.5 h / 0 - 20 °C
4.1: hydrogenchloride; ozone; oxygen / dichloromethane; ethyl acetate / 0.58 h / -78 °C
4.2: 3 h / -78 - 0 °C
5.1: triethylamine; methanesulfonyl chloride / N,N-dimethyl-formamide / 20 °C
5.2: 120 °C
5.3: 40 °C
View Scheme

: (2R,3S)-3-(3-acetoxy-2-methylbenzamido)-1-((3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl)pent-4-en-2-yl-4-methoxybenzoate

: 159989-64-7
nelfinavir

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: hydrogenchloride; ozone; oxygen / dichloromethane; ethyl acetate / 0.58 h / -78 °C 1.2: 3 h / -78 - 0 °C 2.1: triethylamine; methanesulfonyl chloride / N,N-dimethyl-formamide / 0.33 h / 20 °C 2.2: 3 h / 50 °C 3.1: potassium carbonate / methanol / 2 h / 100 °C / Sealed tube 4.1: potassium hydrogencarbonate / 5 h / 140 °C / Sealed tube View Scheme

: (2R,3S)-3-(3-acetoxy-2-methylbenzamido)-1-((3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl)pent-4-en-2-yl-4-methoxybenzoate

A: 159989-64-7
nelfinavir

B: 1025935-06-1
(3S,4aS,8aS)-2-[(2S,3S)-3-Hydroxy-2-(3-hydroxy-2-methyl-benzoylamino)-4-phenylsulfanyl-butyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogenchloride; ozone; oxygen / dichloromethane; ethyl acetate / 0.58 h / -78 °C 1.2: 3 h / -78 - 0 °C 2.1: triethylamine; methanesulfonyl chloride / N,N-dimethyl-formamide / 20 °C 2.2: 120 °C 2.3: 40 °C View Scheme

: C27H41N3O4

: 159989-64-7
nelfinavir

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: triethylamine / dichloromethane / 0.5 h / 0 - 20 °C 2.1: hydrogenchloride; ozone; oxygen / dichloromethane; ethyl acetate / 0.58 h / -78 °C 2.2: 3 h / -78 - 0 °C 3.1: triethylamine; methanesulfonyl chloride / N,N-dimethyl-formamide / 0.33 h / 20 °C 3.2: 3 h / 50 °C 4.1: potassium carbonate / methanol / 2 h / 100 °C / Sealed tube 5.1: potassium hydrogencarbonate / 5 h / 140 °C / Sealed tube View Scheme

Yield

Multi-step reaction with 5 steps
1.1: triethylamine / dichloromethane / 0.5 h / 0 - 20 °C
2.1: hydrogenchloride; ozone; oxygen / dichloromethane; ethyl acetate / 0.58 h / -78 °C
2.2: 3 h / -78 - 0 °C
3.1: triethylamine; methanesulfonyl chloride / N,N-dimethyl-formamide / 0.33 h / 20 °C
3.2: 3 h / 50 °C
4.1: potassium carbonate / methanol / 2 h / 100 °C / Sealed tube
5.1: potassium hydrogencarbonate / 5 h / 140 °C / Sealed tube
View Scheme

: C27H41N3O4

A: 159989-64-7
nelfinavir

B: 1025935-06-1
(3S,4aS,8aS)-2-[(2S,3S)-3-Hydroxy-2-(3-hydroxy-2-methyl-benzoylamino)-4-phenylsulfanyl-butyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 0.5 h / 0 - 20 °C 2.1: hydrogenchloride; ozone; oxygen / dichloromethane; ethyl acetate / 0.58 h / -78 °C 2.2: 3 h / -78 - 0 °C 3.1: triethylamine; methanesulfonyl chloride / N,N-dimethyl-formamide / 20 °C 3.2: 120 °C 3.3: 40 °C View Scheme

: (2R,3S)-3-(3-acetoxy-2-methylbenzamido)-1-((3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl)-4-hydroxybutan-2-yl-4-methoxybenzoate

: 159989-64-7
nelfinavir

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triethylamine; methanesulfonyl chloride / N,N-dimethyl-formamide / 0.33 h / 20 °C 1.2: 3 h / 50 °C 2.1: potassium carbonate / methanol / 2 h / 100 °C / Sealed tube 3.1: potassium hydrogencarbonate / 5 h / 140 °C / Sealed tube View Scheme

: C36H47N3O7

: 159989-64-7
nelfinavir

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / methanol / 2 h / 100 °C / Sealed tube 2: potassium hydrogencarbonate / 5 h / 140 °C / Sealed tube View Scheme

: 75-75-2
methanesulfonic acid

: 159989-64-7
nelfinavir

: 159989-65-8
nelfinavir mesylate

Conditions

Conditions	Yield
In acetone at 20 - 35℃; for 2h; Product distribution / selectivity;	98%
Stage #1: methanesulfonic acid; nelfinavir In methanol at 25 - 30℃; for 0.166667h; Stage #2: In methanol at 25 - 30℃; for 0.25h; Carbon; Stage #3: at 40 - 55℃; under 10 - 150 Torr; for 1h; Product distribution / selectivity;	92%
In ethanol Product distribution / selectivity;	80%

: 67000-01-5
methyltertbutyl ether

: 159989-64-7
nelfinavir

: 159989-65-8
nelfinavir mesylate

Conditions

Conditions	Yield
With methanesulfonic acid In tetrahydrofuran	95%

: 159989-64-7
nelfinavir

: 1,2:5,6-di-O-isopropylidene-3-O-(4-izocyanatobutyl)-α-D-glucofuranose

: [4-[3-O-(1,2:5,6-di-O-isopropylidene-α-D-glucofuranose)]-butyl]carbamic acid 1(R)-[3(S)-tert-butylcarbamoyloctahydro-4a(S),8a(S)-isoquinolin-2-ylmethyl]-2(S)-(3-hydroxy-2-methylbenzoylamino)-3-phenylsulfanylpropyl ester

Conditions

Conditions	Yield
With copper(l) chloride In dichloromethane; N,N-dimethyl-formamide at 20℃;	63.5%

: C22H30N6O4S2

: 159989-64-7
nelfinavir

A: C54H73N9O7S3

B: C54H73N9O7S3

C: C76H101N15O10S5

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; Inert atmosphere; Molecular sieve;	A 62% B 3% C 2%

...Expand

: 159989-64-7
nelfinavir

: 1,2:5,6-di-O-isopropylidene-3-O-(3-carboxypropanoyl)-α-D-glucofuranose

: succinic acid 3-[3-[3(S)-tert-butylcarbamoyloctahydro-4a(S),8a(S)-isoquinolin-2-yl]-2(R)-hydroxy-1(S)-phenylsulfanylmethylpropylcarbamoyl]-2-methylphenyl ester 4-[3-O-(1,2:5,6-di-O-isopropylidene-α-D-glucofuranose)] ester

Conditions

Conditions	Yield
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 0 - 20℃;	16%

: 159989-64-7
nelfinavir

: [4-[3-O-D-glucose]-butyl]carbamic acid 1(R)-[3(S)-tert-butylcarbamoyloctahydro-4a(S),8a(S)-isoquinolin-2-ylmethyl]-2(S)-(3-hydroxy-2-methylbenzoylamino)-3-phenylsulfanylpropyl ester (bis trifluoroacatic acid salt)

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 63.5 percent / CuCl / CH2Cl2; dimethylformamide / 20 °C 2: 97 percent / H2O; acetonitrile / 0 - 20 °C View Scheme

: 7-(3-benzyl-1-ethyl-(1H)-pyrazol-5-yl)-3-azabicyclo[3.3.0]octane

: 159989-64-7
nelfinavir

: 1-(((3S,4S)-3-((7-(3-Benzyl-1-ethyl-(1H)-pyrazol-5-yl)-3-azabicyclo[3.3.0]octan-3-yl)methyl]-4-(3-fluorophenyl)pyrrolidin-1-yl)methyl) cyclohexanecarboxylic Acid

: 159989-64-7
nelfinavir

: 3-({3-[3-(tert-butylaminomethyl)octahydroisoquinolin-2-yl]-2-hydroxy-1-phenylsulfanylmethylpropylamino}methyl)-2-methylphenol

Conditions

Conditions	Yield
Stage #1: nelfinavir With borane-THF In tetrahydrofuran at 65℃; Inert atmosphere; Stage #2: With piperidine In methanol at 65℃; Inert atmosphere;

Nelfinavir Specification

The Nelfinavir, with the CAS registry number 159989-64-7, is also known as 3-Isoquinolinecarboxamide,N-(1,1-dimethylethyl)decahydro-2-[(2R,3R)-2-hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-(phenylthio)butyl]-,(3S,4aS,8aS)-. This chemical's molecular formula is C₃₂H₄₅N₃O₄S and molecular weight is 567.79. What's more, its systematic name is (3S,4aS,8aS)-2-[(2R,3R)-2-Hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-(phenylsulfanyl)butyl]-N-(2-methyl-2-propanyl)decahydro-3-isoquinolinecarboxamide. Its classification codes are: (1)Anti-HIV agents; (2)Anti-Infective Agents; (3)Anti-Retroviral Agents; (4)Antiviral Agents; (5)Enzyme Inhibitors; (6)HIV Protease inhibitors; (7)Protease Inhibitors. This chemical is a potent HIV protease inhibitor. It is used in combination with other antiviral drugs in the treatment of HIV in both adults and children. It belongs to the class of drugs known as protease inhibitors (PIs) and like other PIs is generally used in combination with other antiretroviral drugs.

Physical properties of Nelfinavir are: (1)ACD/LogP: 7.278; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 6.80; (4)ACD/LogD (pH 7.4): 7.26; (5)ACD/BCF (pH 5.5): 66657.38; (6)ACD/BCF (pH 7.4): 193716.50; (7)ACD/KOC (pH 5.5): 72239.41; (8)ACD/KOC (pH 7.4): 209938.70; (9)#H bond acceptors: 7; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 12; (12)Polar Surface Area: 127.2 Å²; (13)Index of Refraction: 1.619; (14)Molar Refractivity: 162.378 cm³; (15)Molar Volume: 463.136 cm³; (16)Polarizability: 64.372×10^-24cm³; (17)Surface Tension: 58.72 dyne/cm; (18)Density: 1.226 g/cm³; (19)Flash Point: 429.665 °C; (20)Enthalpy of Vaporization: 120.056 kJ/mol; (21)Boiling Point: 786.839 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(c1cccc(O)c1C)N[C@@H](CSc2ccccc2)[C@H](O)CN4[C@H](C(=O)NC(C)(C)C)C[C@@H]3CCCC[C@@H]3C4
(2)Std. InChI: InChI=1S/C32H45N3O4S/c1-21-25(15-10-16-28(21)36)30(38)33-26(20-40-24-13-6-5-7-14-24)29(37)19-35-18-23-12-9-8-11-22(23)17-27(35)31(39)34-32(2,3)4/h5-7,10,13-16,22-23,26-27,29,36-37H,8-9,11-12,17-20H2,1-4H3,(H,33,38)(H,34,39)/t22-,23+,26-,27-,29+/m0/s1
(3)Std. InChIKey: QAGYKUNXZHXKMR-HKWSIXNMSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rat	LD	oral	> 5gm/kg (5000mg/kg)		Toxicologist. Vol. 42, Pg. 55, 1998.

Product Name

Nelfinavir

Synthetic route

Nelfinavir Specification

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