tert-Butyl ((2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamate

Base Information

• Chemical Name: tert-Butyl ((2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamate
• CAS No.: 183004-94-6
• Molecular Formula: C25H37N3O5S
• Molecular Weight: 491.652
• DSSTox Substance ID: DTXSID60463596
• Wikidata: Q82288556
• Mol file: 183004-94-6.mol

Synonyms:183004-94-6;tert-Butyl ((2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamate;tert-butyl N-[(2S,3R)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate;[(1S,2R)-1-Benzyl-2-hydroxy-3-[isobutyl-[(4-aminophenyl)sulfonyl]amino] propyl]carbamic Acid tert-Butyl Ester;tert-Butyl ((2S,3R)-4-(4-amino-N-isobutylphenyl-sulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamate;[(1S,2R)-1-Benzyl-2-hydroxy-3-[isobutyl-[(4-aminophenyl)sulfonyl]amino]propyl]carbamic Acid tert-Butyl Ester;SCHEMBL1104910;AMY4341;DTXSID60463596;AKOS016005110;[(1S,2R)-1-Benzyl-2-hydroxy-3-[isobutyl-[(4-aminophenyl)sulfonyl]amino] propyl]-carbamic Acid tert-Butyl Ester;AC-28969;J-011713;Carbamic acid, N-[(1S,2R)-3-[[(4-aminophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]-, 1,1-dimethylethyl ester;tert-Butyl {(2S,3R)-4-[(4-aminobenzene-1-sulfonyl)(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl}carbamate;tert-Butyl((2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamate

Chemical Property of tert-Butyl ((2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamate

Chemical Property:

• Melting Point: 60-63 °C
• Refractive Index: 1.571
• PKA: 11.98±0.46(Predicted)
• PSA: 130.34000
• Density: 1.198 g/cm³
• LogP: 5.46530
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 12
• Exact Mass: 491.24539246
• Heavy Atom Count: 34
• Complexity: 718

Purity/Quality:

99% ^*data from raw suppliers

[(1S,2R)-1-Benzyl-2-hydroxy-3-[isobutyl-[(4-aminophenyl)sulfonyl]amino]propyl]carbamicAcidtert-ButylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CN(CC(C(CC1=CC=CC=C1)NC(=O)OC(C)(C)C)O)S(=O)(=O)C2=CC=C(C=C2)N
• Isomeric SMILES: CC(C)CN(C[C@H]([C@H](CC1=CC=CC=C1)NC(=O)OC(C)(C)C)O)S(=O)(=O)C2=CC=C(C=C2)N
• Uses: Darunavir intermediate, a potent inhibitor of HIV-1 protease

Technology Process of tert-Butyl ((2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamate

There total 16 articles about tert-Butyl ((2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester (191226-98-9) → 3-S-(N-tert-butyloxyformamido)-[2R-hydroxy-1-[(4-aminophenylsulfonyl)(2-methylpropyl)]amino]-4-phenylbutane (183004-94-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 22 - 30 ℃; Product distribution / selectivity;

Reference yield: 94.0%

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile (58632-95-4) + 4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide (169280-56-2) → 3-S-(N-tert-butyloxyformamido)-[2R-hydroxy-1-[(4-aminophenylsulfonyl)(2-methylpropyl)]amino]-4-phenylbutane (183004-94-6)

Guidance literature:

With triethylamine; In tetrahydrofuran; for 16h;

DOI:10.1016/j.bmc.2003.07.001

Reference yield:

2R-hydroxy-3-[[(4-aminophenyl)sulfonyl](2-methylpropyl)amino]-1S-(phenylmethyl)-propylamine + 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile (74651-77-7) → 3-S-(N-tert-butyloxyformamido)-[2R-hydroxy-1-[(4-aminophenylsulfonyl)(2-methylpropyl)]amino]-4-phenylbutane (183004-94-6)

Guidance literature:

With triethylamine; In tetrahydrofuran; dichloromethane;

upstream raw materials:

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

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

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

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

Downstream raw materials:

3-S-amino-2R-hydroxy-1-[(2-aminobenzothiazol-6-sulfonyl)(2-methylpropyl)amino]-4-phenylbutane

[14C]-Darunavir ethanolate

3-S-(N-t-butyloxyformamido)-2R-hydroxy-1-[(2-aminobenzothiazol-6-sulfonyl)(2-methylpropyl)amino]-4-phenylbutane

darunavir