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

Base Information

• Chemical Name: Tert-butyl [(1S,2R)-1-benzyl-2-hydroxy-3-[isobutyl[(4-nitrophenyl)sulfonyl]amino]propyl]carbamate
• CAS No.: 191226-98-9
• Molecular Formula: C25H35N3O7S
• Molecular Weight: 521.635
• European Community (EC) Number: 467-070-6,606-234-5
• DSSTox Substance ID: DTXSID80437719
• Nikkaji Number: J2.018.763H
• Wikidata: Q72502417
• Mol file: 191226-98-9.mol

Synonyms:191226-98-9;tert-Butyl ((2S,3R)-3-hydroxy-4-(N-isobutyl-4-nitrophenylsulfonamido)-1-phenylbutan-2-yl)carbamate;TERT-BUTYL [(1S,2R)-1-BENZYL-2-HYDROXY-3-[ISOBUTYL[(4-NITROPHENYL)SULFONYL]AMINO]PROPYL]CARBAMATE;tert-butyl N-[(2S,3R)-3-hydroxy-4-[2-methylpropyl-(4-nitrophenyl)sulfonylamino]-1-phenylbutan-2-yl]carbamate;[(1S,2R)-1-Benzyl-2-hydroxy-3-[isobutyl[(4-nitro-phenyl)sulfonyl)]amino]propyl]-carbamic Acid tert-Butyl Ester;tert-Butyl ((2S,3R)-3-hydroxy-4-(N-isobutyl-4-nitro-phenylsulfonamido)-1-phenylbutan-2-yl)carbamate;[(1S,2R)-1-Benzyl-2-hydroxy-3-[isobutyl[(4-nitro-phenyl)sulfonyl)]amino]propyl]-carbamic Acid tert-B;tert-Butyl N-[(1S,2R)-1-Benzyl-2-hydroxy-3-[(2-methylpropyl)[(4-nitrophenyl)sulfonyl]amino]propyl]carbamate;tert-butyl (2S,3R)-3-hydroxy-4-(N-isobutyl-4-nitrophenylsulfonamido)-1-phenylbutan-2-ylcarbamate;Carbamic acid, ((1S,2R)-2-hydroxy-3-((2-methylpropyl)((4-nitrophenyl)sulfonyl)amino)-1-(phenylmethyl)propyl)-, 1,1-dimethylethyl ester;Carbamic acid, [(1S,2R)-2-hydroxy-3-[(2-methylpropyl)[(4-nitrophenyl)sulfonyl]amino]-1-(phenylmethyl)propyl]-, 1,1-dimethylethyl ester;SCHEMBL1104908;DTXSID80437719;AKOS015904187;AM84661;AC-27022;tert-butyl ((2S,3R)-3-hydroxy-4-((N-isobutyl-4-nitrophenyl)sulfonamido)-1-phenylbutan-2-yl)carbamate;EC 467-070-6;A880383;J-012358;J-524380;(1S,2R)-{1-benzyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-carbamic acid tert-butyl ester;(1S,2R)-{1-benzyl-2-hydroxy-3-[isobutyl-(4-nitrobenzene sulfonyl)-amino]propyl}-carbamic acid tert-butyl ester;(1S,2R)-tert-butyl N-[1-benzyl-2-hydroxy-3-(N-isobutyl- 4-nitrobenzenesulphonamido)propyl]carbamate;[(1S,2R)-3-[[(4-nitrophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butylester;N-Isobutyl-N-[(2R,3S)-2-hydroxy-3-(tert-butoxycarbonylamino)-4-phenylbutyl]-4-nitrobenzenesulfonamide;t-butyl((1s,2r)-1-benzyl-2-hydroxy-3-[isobutyl[(-4-nitrophenyl)sulfonyl]-amino]propyl]carbamate;tert-Butyl {(2S,3R)-3-hydroxy-4-[(2-methylpropyl)(4-nitrobenzene-1-sulfonyl)amino]-1-phenylbutan-2-yl}carbamate;tert-Butyl((2S,3R)-3-hydroxy-4-(N-isobutyl-4-nitrophenylsulfonamido)-1-phenylbutan-2-yl)carbamate;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

Chemical Property of Tert-butyl [(1S,2R)-1-benzyl-2-hydroxy-3-[isobutyl[(4-nitrophenyl)sulfonyl]amino]propyl]carbamate

Chemical Property:

• Melting Point: 166-168 °C
• Refractive Index: 1.568
• PKA: 11.94±0.46(Predicted)
• PSA: 150.14000
• Density: 1.242 g/cm³
• LogP: 5.73330
• Storage Temp.: Refrigerator
• Solubility.: Acetone, Chloroform, Dichloromethane, Ethyl Acetate
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 12
• Exact Mass: 521.21957164
• Heavy Atom Count: 36
• Complexity: 803

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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+](=O)[O-]
• 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+](=O)[O-]

Technology Process of Tert-butyl [(1S,2R)-1-benzyl-2-hydroxy-3-[isobutyl[(4-nitrophenyl)sulfonyl]amino]propyl]carbamate

There total 22 articles about Tert-butyl [(1S,2R)-1-benzyl-2-hydroxy-3-[isobutyl[(4-nitrophenyl)sulfonyl]amino]propyl]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: 100.0%

4-Nitrobenzenesulfonyl chloride (98-74-8) + (2R,3S)-3-tert-butoxycarbonylamino-1-isobutylamino-4-phenyl-2-butanol (160232-08-6) → [(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester (191226-98-9)

Guidance literature:

With sodium hydrogencarbonate; In dichloromethane; water; at 20 ℃; for 21h;

DOI:10.1002/ejoc.201600062

Reference yield: 92.88%

isobutylamine (78-81-9) + (1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester (98760-08-8,98818-34-9,98818-35-0,103127-56-6,98737-29-2) + 4-Nitrobenzenesulfonyl chloride (98-74-8) → [(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester (191226-98-9)

Guidance literature:

isobutylamine; (1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester; for 3h; Heating;

4-Nitrobenzenesulfonyl chloride; With triethylamine; In dichloromethane; Reflux;

Reference yield:

N-isobutyl-4-nitrobenzenesulfonamide (89840-80-2) + (1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester (98760-08-8,98818-34-9,98818-35-0,103127-56-6,98737-29-2) → [(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester (191226-98-9)

Guidance literature:

With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate; In 1,4-dioxane; at 80 - 85 ℃; for 6h;

upstream raw materials:

4-Nitrobenzenesulfonyl chloride

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

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

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

Downstream raw materials:

1-ethyl-N-((2S,3R)-3-hydroxy-4-(N-isobutyl-4-nitrophenylsulfonamido)-1-phenylbutan-2-yl)cyclopentanecarboxamide

N-((2S,3R)-3-hydroxy-4-(N-isobutyl-4-nitrophenylsulfonamido)-1-phenylbutan-2-yl)-2-((S)-tetrahydrofuran-3-yloxy)acetamide

N-((2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)-2-((S)-tetrahydrofuran-3-yloxy)acetamide

[14C]-Darunavir ethanolate

Refernces

• 1、 Zhu, Mei,Shan, Qi,Ma, Ling,Wen, Jiajia,Dong, Biao,Zhang, Guoning,Wang, Minghua,Wang, Juxian,Zhou, Jinming,Cen, Shan,Wang, Yucheng. "Design and biological evaluation of cinnamic and phenylpropionic amide derivatives as novel dual inhibitors of HIV-1 protease and reverse transcriptase". . . Retrieved 2021/05/04.
• 2、 Girigani, Sathyanarayana,Singh, Harnam,Kola, Sankar Rao,Dayanand Yelmeli, Vijayalaxmi,Regula, Venu Gopal,Shah, Sakshi,Jain, Neelu,Kumar, Pramod. "An improved and robust scale-up process aided with identification and control of critical process impurities in darunavir ethanolate". . p. 267 - 281. Retrieved 2019/08/26.