Product Name

  • Name

    tert-Butyl [(1S,2R)-1-benzyl-2-hydroxy-3-[isobutyl[(4-nitrophenyl)sulfonyl]amino]propyl]carbamate

  • EINECS
  • CAS No. 191226-98-9
  • Article Data32
  • CAS DataBase
  • Density 1.242 g/cm3
  • Solubility
  • Melting Point 166-168 °C
  • Formula C25H35N3O7S
  • Boiling Point
  • Molecular Weight 521.635
  • Flash Point
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 191226-98-9 (tert-Butyl [(1S,2R)-1-benzyl-2-hydroxy-3-[isobutyl[(4-nitrophenyl)sulfonyl]amino]propyl]carbamate)
  • Hazard Symbols
  • Synonyms carbamic acid, N-[(1S,2R)-2-hydroxy-3-[(2-methylpropyl)[(4-nitrophenyl)sulfonyl]amino]-1-(phenylmethyl)propyl]-, 1,1-dimethylethyl ester;tert-Butyl [(2S,3R)-3-hydroxy-4-{isobutyl[(4-nitrophenyl)sulfonyl]amino}-1-phenylbutan-2-yl]carbamate;
  • PSA 150.14000
  • LogP 5.73330

Synthetic route

4-Nitrobenzenesulfonyl chloride
98-74-8

4-Nitrobenzenesulfonyl chloride

(2R,3S)-3-tert-butoxycarbonylamino-1-isobutylamino-4-phenyl-2-butanol
160232-08-6

(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
191226-98-9

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester

Conditions
ConditionsYield
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
78-81-9

isobutylamine

(1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester
98760-08-8, 98818-34-9, 98818-35-0, 103127-56-6, 98737-29-2

(1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester

4-Nitrobenzenesulfonyl chloride
98-74-8

4-Nitrobenzenesulfonyl chloride

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
191226-98-9

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester

Conditions
ConditionsYield
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
98760-08-8, 98818-34-9, 98818-35-0, 103127-56-6, 98737-29-2

(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
191226-98-9

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester

Conditions
ConditionsYield
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
326479-99-6

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
191226-98-9

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester

Conditions
ConditionsYield
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
326480-01-7

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
191226-98-9

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester

Conditions
ConditionsYield
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
357604-37-6

(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
191226-98-9

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester

Conditions
ConditionsYield
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
326480-00-6

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
191226-98-9

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester

Conditions
ConditionsYield
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
357604-36-5

[(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
191226-98-9

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester

Conditions
ConditionsYield
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
357604-38-7

[(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
191226-98-9

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester

Conditions
ConditionsYield
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
326480-02-8

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
191226-98-9

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester

Conditions
ConditionsYield
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
357604-39-8

(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
191226-98-9

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester

Conditions
ConditionsYield
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
1229623-13-5

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
191226-98-9

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester

Conditions
ConditionsYield
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
220871-52-3

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
191226-98-9

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: isopropyl alcohol / 6 h / 80 °C
2: triethylamine / dichloromethane / 12 h / 0 - 20 °C
View Scheme
N-(tert-butoxycarbonyl)-L-phenylalanine chlorohydrine

N-(tert-butoxycarbonyl)-L-phenylalanine chlorohydrine

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
191226-98-9

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydrogencarbonate / dichloromethane / 5 h / Reflux
2: triethylamine / dichloromethane / Reflux
View Scheme
4-Nitrobenzenesulfonyl chloride
98-74-8

4-Nitrobenzenesulfonyl chloride

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
191226-98-9

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester

Conditions
ConditionsYield
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
89840-80-2

N-isobutyl-4-nitrobenzenesulfonamide

(1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester
98760-08-8, 98818-34-9, 98818-35-0, 103127-56-6, 98737-29-2

(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
191226-98-9

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester

Conditions
ConditionsYield
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
165727-45-7

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
191226-98-9

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester

Conditions
ConditionsYield
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+)
910642-68-1

C15H20N3O3(1+)

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
191226-98-9

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester

Conditions
ConditionsYield
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
102123-74-0

(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
191226-98-9

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester

Conditions
ConditionsYield
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
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
191226-98-9

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester

Conditions
ConditionsYield
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
98760-08-8

(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
191226-98-9

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester

Conditions
ConditionsYield
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
191226-98-9

[(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
251105-80-3

N-(3S-amino-2R-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitro-benzenesulfonamide hydrochloride

Conditions
ConditionsYield
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
191226-98-9

[(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
169280-56-2

4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide

Conditions
ConditionsYield
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
191226-98-9

[(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
183004-94-6

3-S-(N-tert-butyloxyformamido)-[2R-hydroxy-1-[(4-aminophenylsulfonyl)(2-methylpropyl)]amino]-4-phenylbutane

Conditions
ConditionsYield
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
144-62-7

oxalic acid

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
191226-98-9

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester

1-benzyl-2-hydroxy-3-([isobutyl-(4-aminobenzenesulfonyl)amino]propyl)carbamic acid tert-butyl ester oxalate

1-benzyl-2-hydroxy-3-([isobutyl-(4-aminobenzenesulfonyl)amino]propyl)carbamic acid tert-butyl ester oxalate

Conditions
ConditionsYield
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
138499-08-8

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
191226-98-9

[(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
160231-69-6

4-nitro-N-((2R(syn),3S)-2-hydroxy-4-phenyl-3-((S)-tetrahydrofuran-3-yloxycarbonylamino)-butyl)-N-isobutylbenzenesulfonamide

Conditions
ConditionsYield
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
191226-98-9

[(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
244634-31-9

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]amine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane at 0 - 20℃;85%
With hydrogenchloride In ethanol80%
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
5070-13-3

bis-(p-nitrophenyl) carbonate

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
191226-98-9

[(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
229495-94-7

Carbonic acid (1R,2S)-2-tert-butoxycarbonylamino-1-{[isobutyl-(4-nitro-benzenesulfonyl)-amino]-methyl}-3-phenyl-propyl ester 4-nitro-phenyl ester

Conditions
ConditionsYield
With lithium hydroxide In N,N-dimethyl-formamide at 20℃; for 2h;80%
Allyl chloroformate
2937-50-0

Allyl chloroformate

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
191226-98-9

[(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
599173-46-3

Carbonic acid allyl ester (1R,2S)-2-tert-butoxycarbonylamino-1-{[isobutyl-(4-nitro-benzenesulfonyl)-amino]-methyl}-3-phenyl-propyl ester

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran at 0 - 20℃;36%
methyl chloroformate
79-22-1

methyl chloroformate

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
191226-98-9

[(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
599173-45-2

Carbonic acid (1R,2S)-2-tert-butoxycarbonylamino-1-{[isobutyl-(4-nitro-benzenesulfonyl)-amino]-methyl}-3-phenyl-propyl ester methyl ester

Conditions
ConditionsYield
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
191226-98-9

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester

C28H39N3O6S

C28H39N3O6S

Conditions
ConditionsYield
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
191226-98-9

[(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 {3-[(4-amino-benzenesulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-amide

2-oxo-3-phenyl-oxazolidine-5-carboxylic acid {3-[(4-amino-benzenesulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-amide

Conditions
ConditionsYield
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
191226-98-9

[(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 {3-[(4-amino-benzenesulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-amide

2-oxo-3-phenyl-oxazolidine-5-carboxylic acid {3-[(4-amino-benzenesulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-amide

Conditions
ConditionsYield
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
191226-98-9

[(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
919081-52-0

2-oxo-3-phenyl-oxazolidine-5-carboxylic acid {1-benzyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-amide

Conditions
ConditionsYield
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
191226-98-9

[(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
919081-33-7

2-oxo-3-phenyl-oxazolidine-5-carboxylic acid {1-benzyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-amide

Conditions
ConditionsYield
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
191226-98-9

[(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 {3-[(4-amino-benzenesulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-amide

3-(3-fluoro-phenyl)-2-oxo-oxazolidine-5-carboxylic acid {3-[(4-amino-benzenesulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-amide

Conditions
ConditionsYield
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
191226-98-9

[(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
919081-34-8

3-(3-fluoro-phenyl)-2-oxo-oxazolidine-5-carboxylic acid {1-benzyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-amide

Conditions
ConditionsYield
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
191226-98-9

[(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
919081-38-2

3-(4-acetyl-phenyl)-2-oxo-oxazolidine-5-carboxylic acid {1-benzyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-amide

Conditions
ConditionsYield
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
191226-98-9

[(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 {3-[(4-amino-benzenesulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-amide

3-(3,4-difluoro-phenyl)-2-oxo-oxazolidine-5-carboxylic acid {3-[(4-amino-benzenesulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-amide

Conditions
ConditionsYield
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
191226-98-9

[(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
919081-37-1

3-(3-acetyl-phenyl)-2-oxo-oxazolidine-5-carboxylic acid {1-benzyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-amide

Conditions
ConditionsYield
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
191226-98-9

[(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 {3-[(4-amino-benzenesulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-amide

3-(3-acetyl-phenyl)-2-oxo-oxazolidine-5-carboxylic acid {3-[(4-amino-benzenesulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-amide

Conditions
ConditionsYield
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
191226-98-9

[(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 {3-[(4-amino-benzenesulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-amide

3-(4-acetyl-phenyl)-2-oxo-oxazolidine-5-carboxylic acid {3-[(4-amino-benzenesulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-amide

Conditions
ConditionsYield
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
191226-98-9

[(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
919081-35-9

3-(3,4-difluoro-phenyl)-2-oxo-oxazolidine-5-carboxylic acid {1-benzyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-amide

Conditions
ConditionsYield
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
191226-98-9

[(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 {3-[(4-amino-benzenesulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-amide

2-oxo-3-(3-trifluoromethyl-phenyl)-oxazolidine-5-carboxylic acid {3-[(4-amino-benzenesulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-amide

Conditions
ConditionsYield
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
191226-98-9

[(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
919081-36-0

2-oxo-3-(3-trifluoromethyl-phenyl)-oxazolidine-5-carboxylic acid {1-benzyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-amide

Conditions
ConditionsYield
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
191226-98-9

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester

(S)-N-{(1S,2R)-3-[(4-Amino-benzenesulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-3-methyl-2-(2-oxo-tetrahydro-pyrimidin-1-yl)-butyramide

(S)-N-{(1S,2R)-3-[(4-Amino-benzenesulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-3-methyl-2-(2-oxo-tetrahydro-pyrimidin-1-yl)-butyramide

Conditions
ConditionsYield
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
191226-98-9

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester

(S)-N-{(1S,2R)-3-[(4-aminobenzenesulfonyl)isobutylamino]-1-benzyl-2-hydroxypropyl}-2-[3-(2-ethylthiazol-4-ylmethyl)-2-oxo-2,3-dihydroimidazol-1-yl]-3-methylbutyramide

(S)-N-{(1S,2R)-3-[(4-aminobenzenesulfonyl)isobutylamino]-1-benzyl-2-hydroxypropyl}-2-[3-(2-ethylthiazol-4-ylmethyl)-2-oxo-2,3-dihydroimidazol-1-yl]-3-methylbutyramide

Conditions
ConditionsYield
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
191226-98-9

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester

(S)-N-{(1S,2R)-3-[(4-aminobenzenesulfonyl)isobutylamino]-1-benzyl-2-hydroxypropyl}-2-[3-(2-ethylthiazol-4-ylmethyl)-2-oxoimidazolidin-1-yl]-3-methylbutyramide

(S)-N-{(1S,2R)-3-[(4-aminobenzenesulfonyl)isobutylamino]-1-benzyl-2-hydroxypropyl}-2-[3-(2-ethylthiazol-4-ylmethyl)-2-oxoimidazolidin-1-yl]-3-methylbutyramide

Conditions
ConditionsYield
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

tert-Butyl [(1S,2R)-1-benzyl-2-hydroxy-3-[isobutyl[(4-nitrophenyl)sulfonyl]amino]propyl]carbamate Chemical Properties

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:  C25H35N3O7
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

tert-Butyl [(1S,2R)-1-benzyl-2-hydroxy-3-[isobutyl[(4-nitrophenyl)sulfonyl]amino]propyl]carbamate Uses

 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.

tert-Butyl [(1S,2R)-1-benzyl-2-hydroxy-3-[isobutyl[(4-nitrophenyl)sulfonyl]amino]propyl]carbamate Specification

 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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