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159989-64-7

Basic Information
CAS No.: 159989-64-7
Name: Nelfinavir
Article Data: 12
Molecular Structure:
Molecular Structure of 159989-64-7 (Nelfinavir)
Formula: C32H45N3O4S
Molecular Weight: 567.793
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;
EINECS: 1533716-785-6
Density: 1.226 g/cm3
Melting Point: 185-186 °C
Boiling Point: 786.839 °C at 760 mmHg
Flash Point: 429.665 °C
Solubility: 7g/L(temperature not stated)
Appearance: white to off-white crystalline powder
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
ConditionsYield
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.
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
ConditionsYield
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; butanone65%
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
ConditionsYield
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
ConditionsYield
In pyridine69%
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%
168899-58-9

3-acetoxy-2-methylbenzoic acid

159989-64-7

nelfinavir

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
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    159989-64-7 Nelfinavir product Name Nelfinavir Synonyms 3-isoquinolinecarboxamide,n-(1,1-dimethylethyl)decahydro-2-(2-hydroxy-3-((3-hy; 8a-bet

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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.