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169280-56-2

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  • High quality 4-Amino-N-((2R,3S)-3-Amino-2-Hydroxy-4-Phenylbutyl)-N-Isobutylbenzenesulfonamide supplier in China

    Cas No: 169280-56-2

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  • CAS NO. 169280-56-2 4-amino-n-[(2r,3s)-3-amino-2-hydroxy-4-phenylbutyl]-n-isobutylbenzene-1-sulfonamide,

    Cas No: 169280-56-2

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

    Cas No: 169280-56-2

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169280-56-2 Usage

Uses

Different sources of media describe the Uses of 169280-56-2 differently. You can refer to the following data:
1. A metabolite of Darunavir.
2. Amprenavir, Darunavir and Fosamprenavir intermediate

Check Digit Verification of cas no

The CAS Registry Mumber 169280-56-2 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,6,9,2,8 and 0 respectively; the second part has 2 digits, 5 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 169280-56:
(8*1)+(7*6)+(6*9)+(5*2)+(4*8)+(3*0)+(2*5)+(1*6)=162
162 % 10 = 2
So 169280-56-2 is a valid CAS Registry Number.
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

169280-56-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

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

1.2 Other means of identification

Product number -
Other names -

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
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More Details:169280-56-2 SDS

169280-56-2Synthetic route

[(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
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

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
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
N-(3-dibenzylamino-2-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitrobenzenesulfonamide
244641-42-7

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

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
With hydrogen; palladium on activated charcoal In methanol at 20℃;95%
With hydrogen; palladium dihydroxide In methanol at 23℃; for 4h; Catalytic hydrogenation; hydrogenolysis;
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

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
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%
4-nitro-N-((2R(syn),3S)-3-(N-benzyloxycarbonylamino)-2-hydroxy-4-phenylbutyl)-N-isobutyl-benzenesulfonamide
159005-59-1

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

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
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

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

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
With hydrogenchloride In methanol; water at 25 - 35℃; Solvent; Reagent/catalyst;89.6%
(2R,3S)-3-benzyloxycarbonylamino-2-hydroxy-1-(N-isobutylamino)-4-phenylbutane
143224-62-8

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

4-Nitrobenzenesulfonyl chloride
98-74-8

4-Nitrobenzenesulfonyl chloride

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: (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

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

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
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

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

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
With hydrogen; palladium on activated charcoal In ethyl acetate
(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-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
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
(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

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
Multi-step reaction with 3 steps
1: 0.88 g / triethylamine / CH2Cl2 / 4 h / 20 °C
2: H2 / Pd(OH)2 on carbon / ethyl acetate / 1 h
3: 0.75 g / trifluoroacetic acid / CH2Cl2 / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: 90 percent / Et3N / CH2Cl2 / 16 h
2: 95 percent / H2 / Pd(OH)2 / ethyl acetate / 4 h
3: 96 percent / TFA / CH2Cl2 / 4 h
View Scheme
Multi-step reaction with 3 steps
1: 96 percent / NaHCO3 / H2O; CH2Cl2 / 12 h / 23 °C
2: 95 percent / H2 / Pd/C / ethyl acetate / 11 h / 23 °C
3: CF3CO2H / CH2Cl2 / 0.67 h / 23 °C
View Scheme
βS--αR-<<(2-methylpropyl)amino>methyl>-benzenepropanol
169331-42-4

βS--αR-<<(2-methylpropyl)amino>methyl>-benzenepropanol

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
Multi-step reaction with 2 steps
1: 79 percent / Et3N / CH2Cl2 / 4 h / 20 °C
2: 95 percent / H2 / Pd/C / methanol / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 94 percent / Et3N / CH2Cl2 / 2 h / 23 °C
2: H2 / Pd(OH)2/C / methanol / 4 h / 23 °C
View Scheme
4-Nitrobenzenesulfonyl chloride
98-74-8

4-Nitrobenzenesulfonyl chloride

sodium-salt of 3-methyl-crotonamide

sodium-salt of 3-methyl-crotonamide

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
Multi-step reaction with 2 steps
1: 79 percent / Et3N / CH2Cl2 / 4 h / 20 °C
2: 95 percent / H2 / Pd/C / methanol / 20 °C
View Scheme
(2R,3S)-3-benzyloxycarbonylamino-2-hydroxy-1-(N-isobutylamino)-4-phenylbutane
143224-62-8

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

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
Multi-step reaction with 2 steps
1: 75 percent / Et3N / CH2Cl2 / 0 - 20 °C
2: 70 percent / H2 / Pd/C / ethyl acetate
View Scheme
4-Nitrobenzenesulfonyl chloride
98-74-8

4-Nitrobenzenesulfonyl chloride

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
Multi-step reaction with 2 steps
1: 75 percent / Et3N / CH2Cl2 / 0 - 20 °C
2: 70 percent / H2 / Pd/C / ethyl acetate
View Scheme
Multi-step reaction with 2 steps
1.1: 3 h / Heating
1.2: Reflux
2.1: hydrogen; triethanolamine / palladium 10% on activated carbon / methanol / 2 h / 40 - 45 °C
2.2: 2 h / Reflux
2.3: 10 h / 20 °C / pH 9 - 10
View Scheme
Multi-step reaction with 4 steps
1.1: 1,4-dioxane / 1 h / 10 - 25 °C
2.1: potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride / 1,4-dioxane / 6 h / 80 - 85 °C
3.1: trifluoroacetic acid / dichloromethane / 2 h / 20 - 25 °C
3.2: pH 8.5 - 9.2
4.1: hydrogen; palladium 10% on activated carbon / ethanol / 0.58 h / 20 - 25 °C / 2068.65 Torr
View Scheme
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
Multi-step reaction with 6 steps
1: 86 percent / KF; O(9)-benzyl-N-(9-anthracenylmethyl)cinchonidium fluoride / tetrahydrofuran / 6 h / -10 °C
2: 85 percent / NaBH4; NiCl2 / methanol / 0.17 h / 0 °C
3: MgSO4
4: NaBH4 / ethanol / 4 h / 0 - 23 °C
5: 94 percent / Et3N / CH2Cl2 / 2 h / 23 °C
6: H2 / Pd(OH)2/C / methanol / 4 h / 23 °C
View Scheme
(2R,3S)-3-(dibenzylamino)-1-nitro-4-phenylbutan-2-ol
244641-41-6

(2R,3S)-3-(dibenzylamino)-1-nitro-4-phenylbutan-2-ol

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
Multi-step reaction with 5 steps
1: 85 percent / NaBH4; NiCl2 / methanol / 0.17 h / 0 °C
2: MgSO4
3: NaBH4 / ethanol / 4 h / 0 - 23 °C
4: 94 percent / Et3N / CH2Cl2 / 2 h / 23 °C
5: H2 / Pd(OH)2/C / methanol / 4 h / 23 °C
View Scheme
(2R,3S)-1-amino-3-(dibenzylamino)-4-phenylbutan-2-ol
170359-24-7

(2R,3S)-1-amino-3-(dibenzylamino)-4-phenylbutan-2-ol

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
Multi-step reaction with 4 steps
1: MgSO4
2: NaBH4 / ethanol / 4 h / 0 - 23 °C
3: 94 percent / Et3N / CH2Cl2 / 2 h / 23 °C
4: H2 / Pd(OH)2/C / methanol / 4 h / 23 °C
View Scheme
(2R,3S)-3-Dibenzylamino-1-[2-methyl-prop-(E)-ylideneamino]-4-phenyl-butan-2-ol

(2R,3S)-3-Dibenzylamino-1-[2-methyl-prop-(E)-ylideneamino]-4-phenyl-butan-2-ol

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
Multi-step reaction with 3 steps
1: NaBH4 / ethanol / 4 h / 0 - 23 °C
2: 94 percent / Et3N / CH2Cl2 / 2 h / 23 °C
3: H2 / Pd(OH)2/C / methanol / 4 h / 23 °C
View Scheme
(2S)-2-[1'(S)-1-azido-2-phenylethyl]oxirane
136465-89-9

(2S)-2-[1'(S)-1-azido-2-phenylethyl]oxirane

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
Multi-step reaction with 3 steps
1: propan-2-ol / 12 h / 80 °C
2: aq. NaHCO3
3: H2 / 10percent Pd/C / ethyl acetate
View Scheme
(2R,3R)-3-azido-4-phenylbutane-1,2-diol
206361-96-8

(2R,3R)-3-azido-4-phenylbutane-1,2-diol

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
Multi-step reaction with 2 steps
1: aq. NaHCO3
2: H2 / 10percent Pd/C / ethyl acetate
View Scheme
[(1S,2R)-3-[(4-aminophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]amine hydrochloride
1415750-61-6

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

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
With sodium hydroxide In ethanol; water at 0 - 7℃; for 4 - 48h; pH=> 12.5;
With sodium carbonate In dichloromethane; water at 20 - 25℃; for 0.333333h;11.2 g
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

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
Multi-step reaction with 3 steps
1.1: sodium hydrogencarbonate / dichloromethane / 5 h / Reflux
2.1: triethylamine / dichloromethane / Reflux
2.2: Reflux
3.1: hydrogen; triethanolamine / palladium 10% on activated carbon / methanol / 2 h / 40 - 45 °C
3.2: 2 h / Reflux
3.3: 10 h / 20 °C / pH 9 - 10
View Scheme
N-(tert-butoxycarbonyl)-L-phenylalanine chlorohydrine

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

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
Multi-step reaction with 4 steps
1: sodium hydrogencarbonate / dichloromethane / 5 h / Reflux
2: triethylamine / dichloromethane / Reflux
3: hydrogen; triethanolamine / palladium 10% on activated carbon / methanol / 2 h / 40 - 45 °C
4: hydrogenchloride; water / 2 h / Reflux
View Scheme
N-isobutyl-4-nitrobenzenesulfonamide
89840-80-2

N-isobutyl-4-nitrobenzenesulfonamide

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
Multi-step reaction with 3 steps
1.1: potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride / 1,4-dioxane / 6 h / 80 - 85 °C
2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 - 25 °C
2.2: pH 8.5 - 9.2
3.1: hydrogen; palladium 10% on activated carbon / ethanol / 0.58 h / 20 - 25 °C / 2068.65 Torr
View Scheme
4-aminobenzenesulfonyl chloride
24939-24-0

4-aminobenzenesulfonyl chloride

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
Multi-step reaction with 3 steps
1.1: 1,4-dioxane / 0.83 h / 5 - 25 °C
2.1: potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride / 1,4-dioxane / 6 h / 80 - 85 °C
3.1: trifluoroacetic acid / dichloromethane / 2 h / 20 - 25 °C
3.2: pH 8.5 - 9
View Scheme
4-amino-N-isobutylbenzenesulfonamide
53668-36-3

4-amino-N-isobutylbenzenesulfonamide

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
Multi-step reaction with 2 steps
1.1: potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride / 1,4-dioxane / 6 h / 80 - 85 °C
2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 - 25 °C
2.2: pH 8.5 - 9
View Scheme
N-(4-Isobutylsulfamoyl-phenyl)-acetamide
72225-62-8

N-(4-Isobutylsulfamoyl-phenyl)-acetamide

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
Multi-step reaction with 2 steps
1.1: potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride / 1,4-dioxane / 14 h / 85 - 90 °C
2.1: hydrogenchloride; water / ethanol / 10 h / 55 - 65 °C
2.2: 0.5 h / 25 - 30 °C / pH 11.5 - 12.5
View Scheme
Multi-step reaction with 4 steps
1.1: potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride / 1,4-dioxane / 14 h / 85 - 90 °C
2.1: trifluoroacetic acid / dichloromethane / 5 h / 20 - 25 °C
2.2: pH 9.11
3.1: hydrogenchloride / water; ethanol / 6.5 h / 60 - 65 °C
4.1: sodium carbonate / dichloromethane; water / 0.33 h / 20 - 25 °C
View Scheme
p-acetylaminobenzenesulfonyl chloride
121-60-8

p-acetylaminobenzenesulfonyl chloride

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
Multi-step reaction with 3 steps
1.1: 1,4-dioxane / 3.58 h / 5 - 25 °C
2.1: potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride / 1,4-dioxane / 14 h / 85 - 90 °C
3.1: hydrogenchloride; water / ethanol / 10 h / 55 - 65 °C
3.2: 0.5 h / 25 - 30 °C / pH 11.5 - 12.5
View Scheme
Multi-step reaction with 5 steps
1.1: 1,4-dioxane / 3.58 h / 5 - 25 °C
2.1: potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride / 1,4-dioxane / 14 h / 85 - 90 °C
3.1: trifluoroacetic acid / dichloromethane / 5 h / 20 - 25 °C
3.2: pH 9.11
4.1: hydrogenchloride / water; ethanol / 6.5 h / 60 - 65 °C
5.1: sodium carbonate / dichloromethane; water / 0.33 h / 20 - 25 °C
View Scheme
tert-butyl (R)-3-((((4-nitrophenoxy)carbonyl)oxy)methyl)piperidine-1-carboxylate

tert-butyl (R)-3-((((4-nitrophenoxy)carbonyl)oxy)methyl)piperidine-1-carboxylate

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

tert-butyl (R)-3-(((((2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamoyl)oxy)methyl)piperidine-1-carboxylate

tert-butyl (R)-3-(((((2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamoyl)oxy)methyl)piperidine-1-carboxylate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 25℃; for 5h; Inert atmosphere;98.2%
C12H15NO7

C12H15NO7

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

(3aS,4S,7aR)-hexahydro-2H-furo[2,3-b]pyran-4-yl-(2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl carbamate
1262482-52-9

(3aS,4S,7aR)-hexahydro-2H-furo[2,3-b]pyran-4-yl-(2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl carbamate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 23℃; for 1h; Inert atmosphere;96%
N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid
84358-13-4

N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid

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

tert-butyl 4-(((2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamoyl)piperidine-1-carboxylate

tert-butyl 4-(((2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamoyl)piperidine-1-carboxylate

Conditions
ConditionsYield
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 25℃; for 8h; Inert atmosphere;95.4%
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

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

darunavir

darunavir

Conditions
ConditionsYield
In dimethyl sulfoxide at 15 - 30℃; Solvent;94%
With triethylamine In dichloromethane at 20℃;90%
With potassium carbonate In Isopropyl acetate; water at 15 - 35℃; for 4h;83.33%
2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile
58632-95-4

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

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

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 triethylamine In tetrahydrofuran for 16h;94%
With triethylamine In tetrahydrofuran for 16h;94%
(3S)-1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid
88495-54-9

(3S)-1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid

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

tert-butyl (S)-3-(((2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamoyl)piperidine-1-carboxylate

tert-butyl (S)-3-(((2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamoyl)piperidine-1-carboxylate

Conditions
ConditionsYield
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 25℃; for 8h; Inert atmosphere;93.4%
C19H20N2O9

C19H20N2O9

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

C35H44N4O9S

C35H44N4O9S

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 25h;90%
7-hydroxy-2-oxo-2H-chromene-3-carboxylic acid
779-27-1

7-hydroxy-2-oxo-2H-chromene-3-carboxylic acid

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

C30H33N3O7S

C30H33N3O7S

Conditions
ConditionsYield
Stage #1: 7-hydroxy-2-oxo-2H-chromene-3-carboxylic acid; 4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 1.16667h; Inert atmosphere;
Stage #2: With dmap In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;
88%
C14H15NO8
1609973-50-3

C14H15NO8

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

C28H39N3O8S
1609973-55-8

C28H39N3O8S

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 30h;85%
tert-butyl (S)-3-((((4-nitrophenoxy)carbonyl)oxy)methyl)piperidine-1-carboxylate

tert-butyl (S)-3-((((4-nitrophenoxy)carbonyl)oxy)methyl)piperidine-1-carboxylate

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

tert-butyl (S)-3-(((((2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamoyl)oxy)methyl)piperidine-1-carboxylate

tert-butyl (S)-3-(((((2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamoyl)oxy)methyl)piperidine-1-carboxylate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 25℃; for 5h; Inert atmosphere;84.9%
2-oxo-2H-benzopyran-6-carboxylic acid
7734-80-7

2-oxo-2H-benzopyran-6-carboxylic acid

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

C30H33N3O6S

C30H33N3O6S

Conditions
ConditionsYield
Stage #1: 2-oxo-2H-benzopyran-6-carboxylic acid; 4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 1.16667h; Inert atmosphere;
Stage #2: With dmap In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;
84%
7-methoxycoumarin-3-carboxylic acid
20300-59-8

7-methoxycoumarin-3-carboxylic acid

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

C31H35N3O7S

C31H35N3O7S

Conditions
ConditionsYield
Stage #1: 7-methoxycoumarin-3-carboxylic acid; 4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 1.16667h; Inert atmosphere;
Stage #2: With dmap In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;
83%
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl-(4-nitrophenyl)carbonic acid
192725-55-6

(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl-(4-nitrophenyl)carbonic acid

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

darunavir

darunavir

Conditions
ConditionsYield
In 1-methyl-pyrrolidin-2-one at -4 - 30℃; for 10h;82.5%
ethanol
64-17-5

ethanol

(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl-(4-nitrophenyl)carbonic acid
192725-55-6

(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl-(4-nitrophenyl)carbonic acid

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

[14C]-Darunavir ethanolate
635728-49-3

[14C]-Darunavir ethanolate

Conditions
ConditionsYield
Stage #1: (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl-(4-nitrophenyl)carbonic acid; 4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide In 1-methyl-pyrrolidin-2-one at -4 - 30℃; for 10h;
Stage #2: ethanol at 45 - 50℃; for 1h;
82.5%
di(succinimido) carbonate
74124-79-1

di(succinimido) carbonate

(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
156928-09-5

(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

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

darunavir

darunavir

Conditions
ConditionsYield
With pyridine; triethylamine; methylamine In ethanol; water; acetonitrile Product distribution / selectivity;81%
With triethylamine; methylamine In ethanol; water; ethyl acetate; acetonitrile71%
Stage #1: di(succinimido) carbonate; (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol With pyridine In acetonitrile at 25 - 30℃; for 1h;
Stage #2: 4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide In acetonitrile at 0 - 5℃; for 0.5h;
Stage #3: With triethylamine; methylamine In acetonitrile at 0 - 30℃;
bis-(p-nitrophenyl) carbonate
5070-13-3

bis-(p-nitrophenyl) carbonate

(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
156928-09-5

(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

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

darunavir

darunavir

Conditions
ConditionsYield
With triethylamine; methylamine In ethanol; water; ethyl acetate; acetonitrile Product distribution / selectivity;81%
dihydrosinapic acid
14897-78-0

dihydrosinapic acid

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

N-((2S,3R)-4-((4-amino-N-isobutylphenyl)sulfonamido)-3-hydroxy-1-phenylbutan-2-yl)-3-(4-hydroxy-3,5-dimethoxyphenyl)propanamide

N-((2S,3R)-4-((4-amino-N-isobutylphenyl)sulfonamido)-3-hydroxy-1-phenylbutan-2-yl)-3-(4-hydroxy-3,5-dimethoxyphenyl)propanamide

Conditions
ConditionsYield
Stage #1: dihydrosinapic acid; 4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 25℃; for 1.16667h; Inert atmosphere;
Stage #2: With dmap In N,N-dimethyl-formamide at 25℃; for 2h; Inert atmosphere;
81%
(3S,7aS,8S)-hexahydro-4H-3,5-methanofuro[2,3-b]pyran-8-yl (4-nitrophenyl)carbonate

(3S,7aS,8S)-hexahydro-4H-3,5-methanofuro[2,3-b]pyran-8-yl (4-nitrophenyl)carbonate

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

(3S,7aS,8S)-hexahydro-4H-3,5-methanofuro[2,3-b]pyran-8-yl ((2S,3R)-4-((4-amino-N-isobutylphenyl)sulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamate

(3S,7aS,8S)-hexahydro-4H-3,5-methanofuro[2,3-b]pyran-8-yl ((2S,3R)-4-((4-amino-N-isobutylphenyl)sulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 23℃; for 144h;80%
With N-ethyl-N,N-diisopropylamine In acetonitrile at 23℃; for 72h; Inert atmosphere;80%
2-amino-6-chloro-9-carboxymethylpurine
149376-70-5

2-amino-6-chloro-9-carboxymethylpurine

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

2-(2-amino-6-chloro-9H-purin-9-yl)-N-((2S,3R)-4-(4-amino-N- isobutylphenylsulfonamido)-3- hydroxy-1-phenylbutan-2-yl)acetamide

2-(2-amino-6-chloro-9H-purin-9-yl)-N-((2S,3R)-4-(4-amino-N- isobutylphenylsulfonamido)-3- hydroxy-1-phenylbutan-2-yl)acetamide

Conditions
ConditionsYield
Stage #1: 2-amino-6-chloro-9-carboxymethylpurine; 4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 1.16667h; Inert atmosphere;
Stage #2: With dmap In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;
80%
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

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

(E)-N-((2S,3R)-4-((4-amino-N-isobutylphenyl)sulfonamido)-3-hydroxy-1-phenylbutan-2-yl)-3-(4-hydroxy-3-methoxyphenyl)acrylamide

(E)-N-((2S,3R)-4-((4-amino-N-isobutylphenyl)sulfonamido)-3-hydroxy-1-phenylbutan-2-yl)-3-(4-hydroxy-3-methoxyphenyl)acrylamide

Conditions
ConditionsYield
Stage #1: (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid; 4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 25℃; for 1.16667h; Inert atmosphere;
Stage #2: With dmap In N,N-dimethyl-formamide at 25℃; for 2h; Inert atmosphere;
80%
(R)-1-Boc-nipecotic acid
163438-09-3

(R)-1-Boc-nipecotic acid

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

tert-butyl (R)-3-(((2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamoyl)piperidine-1-carboxylate

tert-butyl (R)-3-(((2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamoyl)piperidine-1-carboxylate

Conditions
ConditionsYield
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 25℃; for 8h; Inert atmosphere;79.4%
C13H12N2O10
1609973-49-0

C13H12N2O10

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

C27H36N4O10S
1609973-54-7

C27H36N4O10S

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 30h;79%
2-((3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl)acetic acid

2-((3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl)acetic acid

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

N-((2S,3R)-4-((4-amino-N-isobutylphenyl)sulfonamido)-3-hydroxy-1-phenylbutan-2-yl)-2-((3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl)acetamide
1075209-51-6

N-((2S,3R)-4-((4-amino-N-isobutylphenyl)sulfonamido)-3-hydroxy-1-phenylbutan-2-yl)-2-((3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl)acetamide

Conditions
ConditionsYield
Stage #1: 2-((3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl)acetic acid; 4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 23℃; for 0.0833333h;
Stage #2: With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 23℃; for 24h;
79%

169280-56-2Relevant articles and documents

Preparation method of chiral phenbutamol sulfonamide compound, intermediate for preparing chiral phenbutamol sulfonamide compound and preparation method of chiral phenbutamol sulfonamide compound

-

, (2022/04/08)

The invention discloses a preparation method of a chiral phenbutamol sulfonamide compound, which comprises the following steps: carrying out substitution reaction on a compound A, establishing a chiral center by using ketoreductase, and carrying out amidation and Hofmann degradation to obtain the chiral phenbutamol sulfonamide compound, the structural formula of the compound A is as follows: Q1 and Q2 are independently selected from heteroatom groups containing one or more of nitrogen, oxygen and sulfur, or H, or Q1 and Q2 are connected to form a ring, and R1 is selected from alkyl with the carbon atom number of 1-6. The preparation method provided by the invention has the advantages of simple steps, few reaction steps, mild reaction of each step, high safety coefficient and low production cost.

Design and evaluation of novel piperidine HIV-1 protease inhibitors with potency against DRV-resistant variants

Zhu, Mei,Zhou, Huiyu,Ma, Ling,Dong, Biao,Zhou, Jinming,Zhang, Guoning,Wang, Minghua,Wang, Juxian,Cen, Shan,Wang, Yucheng

, (2021/06/02)

A novel class of HIV-1 protease inhibitors with flexible piperidine as the P2 ligand was designed with the aim of improving extensive interactions with the active subsites. Many inhibitors exhibited good to excellent inhibitory effect on enzymatic activity and viral infectivity. In particular, inhibitor 3a with (R)-piperidine-3-carboxamide as the P2 ligand and 4-methoxybenzenesulfonamide as the P2’ ligand showed an enzyme Ki value of 29 pM and antiviral IC50 value of 0.13 nM, more than six-fold enhancement of activity compared to DRV. Furthermore, there was no significant change in potency against DRV-resistant mutations and HIV-1NL4?3 variant for 3a. Besides, inhibitor 3a exhibited potent antiviral activity against subtype C variants with low nanomole EC50 values. In addition, the molecular modeling revealed important hydrogen bonds and other favorable van der Waals interactions with the backbone atoms of the protease and provided insight for designing and optimizing more potent HIV-1 protease inhibitors.

An improved and robust scale-up process aided with identification and control of critical process impurities in darunavir ethanolate

Girigani, Sathyanarayana,Singh, Harnam,Kola, Sankar Rao,Dayanand Yelmeli, Vijayalaxmi,Regula, Venu Gopal,Shah, Sakshi,Jain, Neelu,Kumar, Pramod

, p. 267 - 281 (2019/08/26)

A robust and safe industrial process, including five isolations and drying steps for widely prescribed anti-HIV (protease inhibitor) drug darunavir ethanolate 2, has been developed. A salient feature of this process is the development of procedures enabling the efficient synthesis of multi-kilogram quantity of darunavir ethanolate, and process demonstrations through plant scale preparation are offered where darunavir molecule has been prepared with overall > 70% chemical yield and > 99.8% purity without involving any purification procedure(s), with all possible process impurities below than the desired limit (not more than 0.08%) were isolated, synthesized and characterized. The developed process is entirely robust, very efficient and demonstrated up to kilograms scale.

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