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4-Amino-N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)benzenesulfonamide
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Name

4-Amino-N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)benzenesulfonamide

 EINECS N/A
CAS No. 169280-56-2 Density 1.226 g/cm3
PSA 118.03000 LogP 4.20870
Solubility N/A Melting Point N/A
Formula C20H29N3O3S Boiling Point 609.105 °C at 760 mmHg
Molecular Weight 391.535 Flash Point 322.175 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 169280-56-2 (4-AMINO-N-[(2R,3S)-3-AMINO-2-HYDROXY-4-PHENYLBUTYL]-N-ISOBUTYLBENZENE-1-SULFONAMIDE) Hazard Symbols N/A
Synonyms

Benzenesulfonamide,4-amino-N-(3-amino-2-hydroxy-4-phenylbutyl)-N-(2-methylpropyl)-, [R-(R*,S*)]-;

Article Data 41

4-Amino-N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)benzenesulfonamide Synthetic route

191226-98-9

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

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
183004-94-6

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

169280-56-2

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

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane for 4h;96%
With trifluoroacetic acid In dichloromethane at 23℃; for 0.666667h;
With trifluoroacetic acid In dichloromethane at 20℃;0.75 g
244641-42-7

N-(3-dibenzylamino-2-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitrobenzenesulfonamide

169280-56-2

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

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol at 20℃;95%
With hydrogen; palladium dihydroxide In methanol at 23℃; for 4h; Catalytic hydrogenation; hydrogenolysis;
251105-80-3

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

169280-56-2

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

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 2585.81 Torr; for 2h; Inert atmosphere;94%
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 2585.81 Torr; for 2h;94%
With palladium 10% on activated carbon; hydrogen In methanol at 25℃; under 2585.81 Torr; for 2h;94%
159005-59-1

4-nitro-N-((2R(syn),3S)-3-(N-benzyloxycarbonylamino)-2-hydroxy-4-phenylbutyl)-N-isobutyl-benzenesulfonamide

169280-56-2

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

Conditions
ConditionsYield
With hydrogen; palladium(II) hydroxide/carbon In methanol at 40℃; under 760.051 Torr; for 3.5h;91%
With hydrogen; palladium(II) hydroxide/carbon In methanol at 40℃; under 760.051 Torr; for 3 - 5.5h;90%
Stage #1: 4-nitro-N-((2R(syn),3S)-3-(N-benzyloxycarbonylamino)-2-hydroxy-4-phenylbutyl)-N-isobutyl-benzenesulfonamide With hydrogenchloride; hydrogen; palladium(II) hydroxide/carbon In methanol; water at 40℃; under 760.051 Torr; for 21h;
Stage #2: With sodium hydroxide In water at 4℃; for 5.7h;		71%

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

169280-56-2

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

Conditions
ConditionsYield
With hydrogenchloride In methanol; water at 25 - 35℃; Solvent; Reagent/catalyst;89.6%
143224-62-8

(2R,3S)-3-benzyloxycarbonylamino-2-hydroxy-1-(N-isobutylamino)-4-phenylbutane

98-74-8

4-Nitrobenzenesulfonyl chloride

169280-56-2

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

Conditions
ConditionsYield
Stage #1: (2R,3S)-3-benzyloxycarbonylamino-2-hydroxy-1-(N-isobutylamino)-4-phenylbutane; 4-Nitrobenzenesulfonyl chloride With triethylamine In ethyl acetate at 40℃; for 3h;
Stage #2: With hydrogen; 5% Pd(OH)2/C In methanol at 40℃; under 760.051 Torr; for 5h;		87%

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

169280-56-2

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

Conditions
ConditionsYield
With potassium carbonate In water at 50 - 60℃; for 3h;76.39%

(2R,3S)-N-isobutyl-N-(2-hydroxy-3-azido-4-phenylbutyl)-p-nitrobenzenesulfonylamide

169280-56-2

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

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethyl acetate
98760-08-8, 98818-34-9, 98818-35-0, 103127-56-6, 98737-29-2

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

169280-56-2

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

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: propan-2-ol / 2 h / 80 °C
2: 0.88 g / triethylamine / CH2Cl2 / 4 h / 20 °C
3: H2 / Pd(OH)2 on carbon / ethyl acetate / 1 h
4: 0.75 g / trifluoroacetic acid / CH2Cl2 / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: 97 percent / propan-2-ol / 3 h / 80 °C
2: 90 percent / Et3N / CH2Cl2 / 16 h
3: 95 percent / H2 / Pd(OH)2 / ethyl acetate / 4 h
4: 96 percent / TFA / CH2Cl2 / 4 h
View Scheme
Multi-step reaction with 4 steps
1: 99 percent / propan-2-ol / 6 h / Heating
2: 96 percent / NaHCO3 / H2O; CH2Cl2 / 12 h / 23 °C
3: 95 percent / H2 / Pd/C / ethyl acetate / 11 h / 23 °C
4: CF3CO2H / CH2Cl2 / 0.67 h / 23 °C
View Scheme

4-Amino-N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)benzenesulfonamide Chemical Properties

Molecule structure of 4-Amino-N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide (CAS NO.169280-56-2):

Molecular Weight: 391.5276 g/mol
Molecular Formula:  C20H29N3O3S 
Density: 1.226 g/cm3 
Boiling Point: 609.105 °C at 760 mmHg 
Flash Point: 322.175 °C
Index of Refraction: 1.605
Molar Refractivity: 109.917 cm3
Molar Volume: 319.307 cm3
Polarizability: 43.575×10-24 cm3
Surface Tension: 55.775 dyne/cm 
Enthalpy of Vaporization: 95.139 kJ/mol 
InChI: InChI=1/C20H29N3O3S/c1-15(2)13-23(27(25,26)18-10-8-17(21)9-11-18)14-20(24)19(22)12-16-6-4-3-5-7-16/h3-11,15,19-20,24H,12-14,21-22H2,1-2H3/t19-,20/m0/s1
InChIKey of 4-Amino-N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide (CAS NO.169280-56-2): NUMJNKDUHFCFJO-XJDOXCRVBY

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