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

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

 EINECS N/A
CAS No. 191226-98-9 Density 1.242 g/cm3
PSA 150.14000 LogP 5.73330
Solubility N/A Melting Point 166-168 °C
Formula C25H35N3O7S Boiling Point N/A
Molecular Weight 521.635 Flash Point N/A
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
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 N/A
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;

Article Data 32

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

98-74-8

4-Nitrobenzenesulfonyl chloride

160232-08-6

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

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%
78-81-9

isobutylamine

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

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

98-74-8

4-Nitrobenzenesulfonyl chloride

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

(1-oxiranyl-2-phenylethyl)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
326479-99-6

2(R)-((tert-butyloxycarbonyl)amino)-1,4-dichloro-3(S)-hydroxybutane

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
326480-01-7

N-t-butyloxycarbonyl-2(S)-(1(S)-t-butyldimethylsilyloxy-2-chloroethyl)aziridine

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
357604-37-6

(S)-2-[(S)-2-Chloro-1-(tetrahydro-pyran-2-yloxy)-ethyl]-aziridine-1-carboxylic 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
326480-00-6

2(S)-t-butyldimethylsilyloxy-3(R)-(t-butyloxycarbonyl)amino-1,4-dichlorobutane

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
357604-36-5

[(1R,2S)-3-Chloro-1-chloromethyl-2-(tetrahydro-pyran-2-yloxy)-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
357604-38-7

[(1S,2S)-1-Benzyl-3-chloro-2-(tetrahydro-pyran-2-yloxy)-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
326480-02-8

2(S)-t-butyldimethylsilyloxy-3(S)-(t-butyloxycarbonyl)amino-1-chloro-4-phenylbutane

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

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:  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

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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