4-Nitrobenzenesulfonyl chloride
(2R,3S)-3-tert-butoxycarbonylamino-1-isobutylamino-4-phenyl-2-butanol
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In dichloromethane; water at 20℃; for 21h; | 100% |
With dmap; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 25℃; for 4h; | 98.2% |
With sodium hydrogencarbonate In dichloromethane; water at 23℃; for 12h; | 96% |
isobutylamine
(1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester
4-Nitrobenzenesulfonyl chloride
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Stage #1: isobutylamine; (1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester for 3h; Heating; Stage #2: 4-Nitrobenzenesulfonyl chloride With triethylamine In dichloromethane Reflux; | 92.88% |
(1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: ethanol / 3 h / 80 °C 2: aq. Na2CO3 / CH2Cl2 / 0 - 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: propan-2-ol / 2 h / 80 °C 2: 0.88 g / triethylamine / CH2Cl2 / 4 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: 97 percent / propan-2-ol / 3 h / 80 °C 2: 90 percent / Et3N / CH2Cl2 / 16 h View Scheme |
2(R)-((tert-butyloxycarbonyl)amino)-1,4-dichloro-3(S)-hydroxybutane
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: p-TsOH*H2O / CH2Cl2 2.1: NaH / tetrahydrofuran 3.1: CuBr*SMe2 / tetrahydrofuran 4.1: p-TsOH*H2O 4.2: KOH / methanol 5.1: 90 percent / propan-2-ol / 5 h / 50 °C 6.1: 88 percent / Et3N / CH2Cl2 / 12 h / 20 °C View Scheme | |
Multi-step reaction with 6 steps 1: 100 percent / imidazole; DMAP / dimethylformamide / 12 h / 50 °C 2: 100 percent / NaH / tetrahydrofuran / 5 h / 0 °C 3: 75 percent / CuBr*Me2S / toluene; tetrahydrofuran / -78 - -20 °C 4: Bu4NF / tetrahydrofuran 5: 90 percent / propan-2-ol / 5 h / 50 °C 6: 88 percent / Et3N / CH2Cl2 / 12 h / 20 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: 100 percent / imidazole; DMAP / dimethylformamide / 12 h / 50 °C 2.1: 100 percent / NaH / tetrahydrofuran / 5 h / 0 °C 3.1: 82 percent / Et3N / methanol / 18 h / 20 °C 4.1: TBAF / tetrahydrofuran / 0.67 h / 20 °C 4.2: 75 percent / KOH / methanol / 2 h / 20 °C 5.1: 90 percent / propan-2-ol / 5 h / 50 °C 6.1: 88 percent / Et3N / CH2Cl2 / 12 h / 20 °C View Scheme |
N-t-butyloxycarbonyl-2(S)-(1(S)-t-butyldimethylsilyloxy-2-chloroethyl)aziridine
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 75 percent / CuBr*Me2S / toluene; tetrahydrofuran / -78 - -20 °C 2: Bu4NF / tetrahydrofuran 3: 90 percent / propan-2-ol / 5 h / 50 °C 4: 88 percent / Et3N / CH2Cl2 / 12 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: 82 percent / Et3N / methanol / 18 h / 20 °C 2.1: TBAF / tetrahydrofuran / 0.67 h / 20 °C 2.2: 75 percent / KOH / methanol / 2 h / 20 °C 3.1: 90 percent / propan-2-ol / 5 h / 50 °C 4.1: 88 percent / Et3N / CH2Cl2 / 12 h / 20 °C View Scheme |
(S)-2-[(S)-2-Chloro-1-(tetrahydro-pyran-2-yloxy)-ethyl]-aziridine-1-carboxylic acid tert-butyl ester
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: CuBr*SMe2 / tetrahydrofuran 2.1: p-TsOH*H2O 2.2: KOH / methanol 3.1: 90 percent / propan-2-ol / 5 h / 50 °C 4.1: 88 percent / Et3N / CH2Cl2 / 12 h / 20 °C View Scheme |
2(S)-t-butyldimethylsilyloxy-3(R)-(t-butyloxycarbonyl)amino-1,4-dichlorobutane
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 100 percent / NaH / tetrahydrofuran / 5 h / 0 °C 2: 75 percent / CuBr*Me2S / toluene; tetrahydrofuran / -78 - -20 °C 3: Bu4NF / tetrahydrofuran 4: 90 percent / propan-2-ol / 5 h / 50 °C 5: 88 percent / Et3N / CH2Cl2 / 12 h / 20 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: 100 percent / NaH / tetrahydrofuran / 5 h / 0 °C 2.1: 82 percent / Et3N / methanol / 18 h / 20 °C 3.1: TBAF / tetrahydrofuran / 0.67 h / 20 °C 3.2: 75 percent / KOH / methanol / 2 h / 20 °C 4.1: 90 percent / propan-2-ol / 5 h / 50 °C 5.1: 88 percent / Et3N / CH2Cl2 / 12 h / 20 °C View Scheme |
[(1R,2S)-3-Chloro-1-chloromethyl-2-(tetrahydro-pyran-2-yloxy)-propyl]-carbamic acid tert-butyl ester
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: NaH / tetrahydrofuran 2.1: CuBr*SMe2 / tetrahydrofuran 3.1: p-TsOH*H2O 3.2: KOH / methanol 4.1: 90 percent / propan-2-ol / 5 h / 50 °C 5.1: 88 percent / Et3N / CH2Cl2 / 12 h / 20 °C View Scheme |
[(1S,2S)-1-Benzyl-3-chloro-2-(tetrahydro-pyran-2-yloxy)-propyl]-carbamic acid tert-butyl ester
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: p-TsOH*H2O 1.2: KOH / methanol 2.1: 90 percent / propan-2-ol / 5 h / 50 °C 3.1: 88 percent / Et3N / CH2Cl2 / 12 h / 20 °C View Scheme |
2(S)-t-butyldimethylsilyloxy-3(S)-(t-butyloxycarbonyl)amino-1-chloro-4-phenylbutane
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: Bu4NF / tetrahydrofuran 2: 90 percent / propan-2-ol / 5 h / 50 °C 3: 88 percent / Et3N / CH2Cl2 / 12 h / 20 °C View Scheme |
(3S)-t-butyldimethylsilyloxy-(2R)-(t-butyloxycarbonyl)amino-4-chloro-1-phenylthiobutane
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: TBAF / tetrahydrofuran / 0.67 h / 20 °C 1.2: 75 percent / KOH / methanol / 2 h / 20 °C 2.1: 90 percent / propan-2-ol / 5 h / 50 °C 3.1: 88 percent / Et3N / CH2Cl2 / 12 h / 20 °C View Scheme |
tert-butyl ((2S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium hydrogencarbonate / dichloromethane / 5 h / Reflux 2.1: triethylamine / dichloromethane / Reflux 2.2: Reflux View Scheme |
1(R,S)-<1'-(S)-<(tert-butyloxycarbonyl)amino>-2-phenylethyl>oxirane
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: isopropyl alcohol / 6 h / 80 °C 2: triethylamine / dichloromethane / 12 h / 0 - 20 °C View Scheme |
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate / dichloromethane / 5 h / Reflux 2: triethylamine / dichloromethane / Reflux View Scheme |
4-Nitrobenzenesulfonyl chloride
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1,4-dioxane / 1 h / 10 - 25 °C 2: potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride / 1,4-dioxane / 6 h / 80 - 85 °C View Scheme |
N-isobutyl-4-nitrobenzenesulfonamide
(1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In 1,4-dioxane at 80 - 85℃; for 6h; | 10 g |
tert-butyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium carbonate / water / 3 h / 60 - 65 °C 2: triethylamine / dichloromethane / 40 - 45 °C View Scheme | |
Multi-step reaction with 2 steps 1: potassium hydroxide / ethanol / 15 - 20 °C / Large scale 2: triethylamine / isopropyl alcohol / 40 - 60 °C / Large scale View Scheme |
C15H20N3O3(1+)
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: hydrogenchloride 2: aluminum isopropoxide / isopropyl alcohol / 3 h / Reflux 3: sodium carbonate / water / 3 h / 60 - 65 °C 4: triethylamine / dichloromethane / 40 - 45 °C View Scheme |
(S)-tert-butyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: aluminum isopropoxide / isopropyl alcohol / 3 h / Reflux 2: sodium carbonate / water / 3 h / 60 - 65 °C 3: triethylamine / dichloromethane / 40 - 45 °C View Scheme | |
Multi-step reaction with 3 steps 1: aluminum isopropoxide / isopropyl alcohol / 3 h / Reflux 2: sodium carbonate / water / 3 h / 60 - 65 °C 3: triethylamine / dichloromethane / 40 - 45 °C View Scheme | |
Multi-step reaction with 3 steps 1: aluminum sec-butoxide / toluene; 2-methyl-propan-1-ol / 15 - 20 °C / Large scale 2: potassium hydroxide / ethanol / 15 - 20 °C / Large scale 3: triethylamine / isopropyl alcohol / 40 - 60 °C / Large scale View Scheme |
N-tert-butoxycarbonyl-L-phenylalanine
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: triethylamine 2: aluminum sec-butoxide / toluene; 2-methyl-propan-1-ol / 15 - 20 °C / Large scale 3: potassium hydroxide / ethanol / 15 - 20 °C / Large scale 4: triethylamine / isopropyl alcohol / 40 - 60 °C / Large scale View Scheme |
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: isopropyl alcohol / 20 - 30 °C 2: triethylamine / dichloromethane / 15 - 25 °C View Scheme |
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
N-(3S-amino-2R-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitro-benzenesulfonamide hydrochloride
Conditions | Yield |
---|---|
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 3h; | 100% |
With trifluoroacetic acid In dichloromethane for 3h; | 83% |
With trifluoroacetic acid In dichloromethane at 25℃; for 2h; | 69.2% |
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide
Conditions | Yield |
---|---|
Stage #1: [(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester With palladium 10% on activated carbon; ammonium formate; acetic acid In tetrahydrofuran at 15 - 20℃; Large scale; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 35 - 45℃; Large scale; | 99.4% |
Stage #1: [(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester With triethanolamine; hydrogen; palladium 10% on activated carbon In methanol at 40 - 45℃; for 2h; Stage #2: With hydrogenchloride; water for 2h; Reflux; Stage #3: With sodium hydroxide In water; isopropyl alcohol at 20℃; for 10h; pH=9 - 10; | 95% |
Multi-step reaction with 2 steps 1: 95 percent / H2 / Pd/C / ethyl acetate / 11 h / 23 °C 2: CF3COOH / CH2Cl2 / 0.67 h / 23 °C View Scheme |
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
3-S-(N-tert-butyloxyformamido)-[2R-hydroxy-1-[(4-aminophenylsulfonyl)(2-methylpropyl)]amino]-4-phenylbutane
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In ethanol at 22 - 30℃; Product distribution / selectivity; | 97% |
With hydrogen; palladium dihydroxide In ethyl acetate for 4h; | 95% |
With hydrogen; palladium on activated charcoal In ethyl acetate at 23℃; for 11h; | 95% |
oxalic acid
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Stage #1: [(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester With hydrogen In isopropyl alcohol at 25 - 35℃; under 3750.38 - 4500.45 Torr; Stage #2: oxalic acid In toluene at 0 - 30℃; for 3h; Solvent; Reagent/catalyst; | 90% |
1-({[(3S)-tetrahydro-3-furanyloxy]carbonyl}oxy)-2,5-pyrrolidinedione
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
4-nitro-N-((2R(syn),3S)-2-hydroxy-4-phenyl-3-((S)-tetrahydrofuran-3-yloxycarbonylamino)-butyl)-N-isobutylbenzenesulfonamide
Conditions | Yield |
---|---|
Stage #1: [(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester With hydrogenchloride In dichloromethane for 1.5h; Stage #2: 1-({[(3S)-tetrahydro-3-furanyloxy]carbonyl}oxy)-2,5-pyrrolidinedione With triethylamine In dichloromethane at 20℃; for 4h; Further stages.; | 85% |
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]amine hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane at 0 - 20℃; | 85% |
With hydrogenchloride In ethanol | 80% |
With hydrogenchloride In ethanol; water at 75 - 80℃; for 1h; | 173 g |
With hydrogenchloride In ethanol; dichloromethane; water at 5 - 80℃; for 2h; Solvent; | 330 g |
bis-(p-nitrophenyl) carbonate
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
Carbonic acid (1R,2S)-2-tert-butoxycarbonylamino-1-{[isobutyl-(4-nitro-benzenesulfonyl)-amino]-methyl}-3-phenyl-propyl ester 4-nitro-phenyl ester
Conditions | Yield |
---|---|
With lithium hydroxide In N,N-dimethyl-formamide at 20℃; for 2h; | 80% |
Allyl chloroformate
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
Carbonic acid allyl ester (1R,2S)-2-tert-butoxycarbonylamino-1-{[isobutyl-(4-nitro-benzenesulfonyl)-amino]-methyl}-3-phenyl-propyl ester
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran at 0 - 20℃; | 36% |
methyl chloroformate
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
Carbonic acid (1R,2S)-2-tert-butoxycarbonylamino-1-{[isobutyl-(4-nitro-benzenesulfonyl)-amino]-methyl}-3-phenyl-propyl ester methyl ester
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran at 0 - 20℃; for 3h; | 13% |
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 95 percent / H2 / Pd/C / ethyl acetate / 11 h / 23 °C 2: CF3COOH / CH2Cl2 / 0.67 h / 23 °C 3: 75 percent / iPr2NEt / acetonitrile / 8 h / 23 °C View Scheme |
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: TFA / CH2Cl2 / 1 h 2: Et3N / tetrahydrofuran / 20 °C 3: SnCl2*2H2O / ethyl acetate / 80 °C View Scheme |
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: TFA / CH2Cl2 / 1 h 2: Et3N / tetrahydrofuran / 20 °C 3: SnCl2*2H2O / ethyl acetate / 80 °C View Scheme |
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
2-oxo-3-phenyl-oxazolidine-5-carboxylic acid {1-benzyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-amide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: TFA / CH2Cl2 / 1 h 2: Et3N / tetrahydrofuran / 20 °C View Scheme |
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
2-oxo-3-phenyl-oxazolidine-5-carboxylic acid {1-benzyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-amide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: TFA / CH2Cl2 / 1 h 2: Et3N / tetrahydrofuran / 20 °C View Scheme |
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: TFA / CH2Cl2 / 1 h 2: Et3N / tetrahydrofuran / 20 °C 3: SnCl2*2H2O / ethyl acetate / 80 °C View Scheme |
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
3-(3-fluoro-phenyl)-2-oxo-oxazolidine-5-carboxylic acid {1-benzyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-amide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: TFA / CH2Cl2 / 1 h 2: Et3N / tetrahydrofuran / 20 °C View Scheme |
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
3-(4-acetyl-phenyl)-2-oxo-oxazolidine-5-carboxylic acid {1-benzyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-amide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: TFA / CH2Cl2 / 1 h 2: Et3N / tetrahydrofuran / 20 °C View Scheme |
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: TFA / CH2Cl2 / 1 h 2: Et3N / tetrahydrofuran / 20 °C 3: SnCl2*2H2O / ethyl acetate / 80 °C View Scheme |
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
3-(3-acetyl-phenyl)-2-oxo-oxazolidine-5-carboxylic acid {1-benzyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-amide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: TFA / CH2Cl2 / 1 h 2: Et3N / tetrahydrofuran / 20 °C View Scheme |
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: TFA / CH2Cl2 / 1 h 2: Et3N / tetrahydrofuran / 20 °C 3: SnCl2*2H2O / ethyl acetate / 80 °C View Scheme |
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: TFA / CH2Cl2 / 1 h 2: Et3N / tetrahydrofuran / 20 °C 3: SnCl2*2H2O / ethyl acetate / 80 °C View Scheme |
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
3-(3,4-difluoro-phenyl)-2-oxo-oxazolidine-5-carboxylic acid {1-benzyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-amide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: TFA / CH2Cl2 / 1 h 2: Et3N / tetrahydrofuran / 20 °C View Scheme |
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: TFA / CH2Cl2 / 1 h 2: Et3N / tetrahydrofuran / 20 °C 3: SnCl2*2H2O / ethyl acetate / 80 °C View Scheme |
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
2-oxo-3-(3-trifluoromethyl-phenyl)-oxazolidine-5-carboxylic acid {1-benzyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-amide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: TFA / CH2Cl2 / 1 h 2: Et3N / tetrahydrofuran / 20 °C View Scheme |
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: H2 / Pd(OH)2 on carbon / ethyl acetate / 1 h 2: 0.75 g / trifluoroacetic acid / CH2Cl2 / 20 °C 3: 45 percent / 3-dimethoxyphosphoryloxy-1,2,3-benzotriazine-4(3H)-one; triethylamine / tetrahydrofuran / 4 h View Scheme |
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: H2 / Pd(OH)2 on carbon / ethyl acetate / 1 h 2: 0.75 g / trifluoroacetic acid / CH2Cl2 / 20 °C 3: 51 percent / N-hydroxysuccinimide; 1,3-dicyclohexylcarbodiimide; N-methylmorpholine / CH2Cl2 / 18 h View Scheme |
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: H2 / Pd(OH)2 on carbon / ethyl acetate / 1 h 2: 0.75 g / trifluoroacetic acid / CH2Cl2 / 20 °C 3: N-hydroxysuccinimide; 1,3-dicyclohexylcarbodiimide; N-methylmorpholine / CH2Cl2 / 18 h View Scheme |
Molecule structure of Carbamic acid,N-[(1S,2R)-2-hydroxy-3-[(2-methylpropyl)[(4-nitrophenyl)sulfonyl]amino]-1-(phenylmethyl)propyl]-,1,1-dimethylethyl ester (CAS NO.191226-98-9):
Molecular Weight: 521.6263 g/mol
Molecular Formula: C25H35N3O7S
Density: 1.242 g/cm3
Melting Point: 166-168 °C
Index of Refraction: 1.568
Molar Refractivity: 137.378 cm3
Molar Volume: 420.071 cm3
Polarizability: 54.461×10-24 cm3
Surface Tension: 50.964 dyne/cm
InChI: InChI=1/C25H35N3O7S/c1-18(2)16-27(36(33,34)21-13-11-20(12-14-21)28(31)32)17-23(29)22(15-19-9-7-6-8-10-19)26-24(30)35-25(3,4)5/h6-14,18,22-23,29H,15-17H2,1-5H3,(H,26,30)/t22-,23+/m0/s1
InChIKey: CQGKCZKCWMWXQP-XZOQPEGZBV
Product Categories: Chiral Reagents; Intermediates; Isotope Labeled Compounds; Sulfur & Selenium Compounds
Carbamic acid,N-[(1S,2R)-2-hydroxy-3-[(2-methylpropyl)[(4-nitrophenyl)sulfonyl]amino]-1-(phenylmethyl)propyl]-,1,1-dimethylethyl ester (CAS NO.191226-98-9) is used as a intermediate in the synthesis of Amprenavir, a selective HIV protease inhibitor.
Carbamic acid,N-[(1S,2R)-2-hydroxy-3-[(2-methylpropyl)[(4-nitrophenyl)sulfonyl]amino]-1-(phenylmethyl)propyl]-,1,1-dimethylethyl ester (CAS NO.191226-98-9) is also named as [(1S,2R)-1-Benzyl-2-hydroxy-3-[isobutyl[(4-nitro-phenyl)sulfonyl)]amino]propyl]-carbamic Acid tert-Butyl Ester ; N-[(1S,2R)-2-Hydroxy-3-[(2-methylpropyl)[(4-nitrophenyl)sulfonyl]amino]-1-(phenylmethyl)propyl]-carbamic Acid 1,1-Dimethylethyl Ester ; tert-Butyl (2S,3R)-3-hydroxy-4-(N-isobutyl-4-nitrophenylsulfonamido)-1-phenylbutan-2-ylcarbamate ; tert-Butyl [(1S,2R)-1-benzyl-2-hydroxy-3-[isobutyl[(4-nitrophenyl)sulfonyl]amino]propyl]carbamate . Carbamic acid,N-[(1S,2R)-2-hydroxy-3-[(2-methylpropyl)[(4-nitrophenyl)sulfonyl]amino]-1-(phenylmethyl)propyl]-,1,1-dimethylethyl ester (CAS NO.191226-98-9) is white solid.
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