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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
NELFINAVIR CAS:159989-64-7 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical intermediates, specializing in high quality organic intermediates
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thiophenol
(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
nelfinavir
B
(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 | 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. |
thiophenol
(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
nelfinavir
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% |
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% |
thiophenol
butanone
(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
nelfinavir
Conditions | Yield |
---|---|
In pyridine | 69% |
(3S,4aS,8aS)-N-tert-butyl-decahydroisoquinoline-3-carboxamide
Acetic acid 3-((1R,2S)-2,3-dihydroxy-1-phenylsulfanylmethyl-propylcarbamoyl)-2-methyl-phenyl ester
nelfinavir
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% |
nelfinavir
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; |
thiophenol
A
nelfinavir
B
(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 | 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% |
3-acetoxy-2-methylbenzoic acid
nelfinavir
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 |
nelfinavir
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 |
nelfinavir
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 |
Acetic acid 3-[(R)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-phenylsulfanyl-ethylcarbamoyl]-2-methyl-phenyl ester
nelfinavir
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 100 percent / HCl / methanol / 3 h / 40 °C 2: 59 percent / TsCl; Et3N View Scheme |
(3S,4aS,8aS)-N-tert-butyl-decahydroisoquinoline-3-carboxamide
nelfinavir
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 |
Acetic acid 3-{(S)-4-[(S)-1-hydroxy-2-(toluene-4-sulfonyloxy)-ethyl]-4,5-dihydro-oxazol-2-yl}-2-methyl-phenyl ester
nelfinavir
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: K2CO3 / propan-2-ol / Heating View Scheme |
3-acetoxy-2-methylbenzoyl chloride
nelfinavir
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 |
(2R)-1-acetoxy-2-((4S)-2-(3-acetoxy-2-methylphenyl)-4,5-dihydrooxazol-4-yl)-2-methanesulfonyloxyethane
nelfinavir
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 |
Acetic acid 3-((5S,6R)-6-hydroxy-2,2-dimethyl-[1,3]dioxepan-5-ylcarbamoyl)-2-methyl-phenyl ester
nelfinavir
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 |
Acetic acid 3-((5S,6R)-6-methanesulfonyloxy-2,2-dimethyl-[1,3]dioxepan-5-ylcarbamoyl)-2-methyl-phenyl ester
nelfinavir
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 |
3-acetoxy-2-methylbenzoyl chloride
(3S,4aS,8aS)-N-tert-butyl-2-[(2R,3R)-3-benzyloxycarbonylamino-2-hydroxy-4-(phenylthio)butyl]decahydroisoquinoline-3-carboxamide
nelfinavir
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; |
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 |
nelfinavir
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 |
A
nelfinavir
B
(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 | 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 |
(3S,4aS,8aS)-N-tert-butyl-decahydroisoquinoline-3-carboxamide
A
nelfinavir
B
(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 | 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 |
nelfinavir
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 |
A
nelfinavir
B
(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 | 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 |
nelfinavir
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 |
A
nelfinavir
B
(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 | 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 |
nelfinavir
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 |
nelfinavir
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 |
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% |
Conditions | Yield |
---|---|
With methanesulfonic acid In tetrahydrofuran | 95% |
nelfinavir
Conditions | Yield |
---|---|
With copper(l) chloride In dichloromethane; N,N-dimethyl-formamide at 20℃; | 63.5% |
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% |
nelfinavir
Conditions | Yield |
---|---|
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 0 - 20℃; | 16% |
nelfinavir
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 |
nelfinavir
nelfinavir
Conditions | Yield |
---|---|
Stage #1: nelfinavir With borane-THF In tetrahydrofuran at 65℃; Inert atmosphere; Stage #2: With piperidine In methanol at 65℃; Inert atmosphere; |
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