(2,5-Dioxopyrrolidin-1-yl) 3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate

Base Information

• Chemical Name: (2,5-Dioxopyrrolidin-1-yl) 3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate
• CAS No.: 3392-08-3
• Molecular Formula: C15H24 N2 O6
• Molecular Weight: 328.365
• Hs Code.: 2925190090
• European Community (EC) Number: 222-231-8
• Mol file: 3392-08-3.mol

Synonyms:Boc-Ile-OSu;3392-08-3;MFCD00022585;Boc-L-isoleucine hydroxysuccinimide ester;SCHEMBL5696168;EINECS 222-231-8;AKOS015842737;NSC 334339;(2,5-dioxopyrrolidin-1-yl) 3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate;SY075030;FT-0634825;Succinimido N-(tert-butoxycarbonyl)isoleucinate;(2,5-Dioxopyrrolidin-1-yl) (2S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate

Chemical Property of (2,5-Dioxopyrrolidin-1-yl) 3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate

Chemical Property:

• Melting Point: 103-108 °C
• PKA: 10.81±0.46(Predicted)
• PSA: 102.01000
• Density: 1.2g/cm³
• LogP: 1.86180
• Storage Temp.: −20°C
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 328.16343649
• Heavy Atom Count: 23
• Complexity: 481

Purity/Quality:

99% ^*data from raw suppliers

Boc-L-isoleucine N-hydroxysuccinimide ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC(C)C(C(=O)ON1C(=O)CCC1=O)NC(=O)OC(C)(C)C
• Uses: Boc-Ile-OSu is used in preparation of Dipeptide Piperidine derivatives for treating or preventing a disease associated with arginase activity.

Technology Process of (2,5-Dioxopyrrolidin-1-yl) 3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate

There total 7 articles about (2,5-Dioxopyrrolidin-1-yl) 3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate 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: 96.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + N-tert-butyloxy-isoleucine (13139-16-7,35264-07-4,55721-65-8,55780-90-0,116194-21-9) → tert-(butoxycarbonyl)isoleucine succinimidyl ester (3392-08-3)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; for 18h; Ambient temperature;

DOI:10.1021/jm00113a025

Reference yield: 90.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + N-(tert-butyloxycarbonyl)-L-isoleucine (13139-16-7) → N-(tert-butoxy)carbonyl-L-isoleucine N-hydroxysuccinimide ester (3392-08-3)

Guidance literature:

With dicyclohexyl-carbodiimide; In ethyl acetate; for 16h;

DOI:10.1002/ardp.200300765

Reference yield: 60.0%

N-(tert-butyloxycarbonyl)-L-isoleucine (13139-16-7) + Isopropenyl Succinimido Carbonate (96935-01-2) → N-(tert-butoxy)carbonyl-L-isoleucine N-hydroxysuccinimide ester (3392-08-3)

Guidance literature:

With 4-methyl-morpholine; In acetonitrile;

DOI:10.1016/S0040-4039(00)98321-7

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

N-tert-butyloxy-isoleucine

N-(tert-butyloxycarbonyl)-L-isoleucine

Isopropenyl Succinimido Carbonate

Downstream raw materials:

BOC-Ile-Gly-OMe

2-((2S,3S)-2-((tert-butoxycarbonyl)amino)-3-methylpentanamido)acetic acid

[(S)-1-((S)-1-Carbamoyl-2-phenyl-ethylcarbamoyl)-2-methyl-butyl]-carbamic acid tert-butyl ester

((1S,2S)-1-{3,5-Bis-[((2S,3S)-2-tert-butoxycarbonylamino-3-methyl-pentanoylamino)-methyl]-benzylcarbamoyl}-2-methyl-butyl)-carbamic acid tert-butyl ester

Refernces

• 1、 Koplūnait?, Martyna,Butkut?, Kamil?,Me?kys, Rolandas,Taurait?, Daiva. "Synthesis of pyrimidine nucleoside and amino acid conjugates". supporting information. . Retrieved 2020/11/13.
• 2、 Tereshchenkov, Andrey G.,Dobosz-Bartoszek, Malgorzata,Osterman, Ilya A.,Marks, James,Sergeeva, Vasilina A.,Kasatsky, Pavel,Komarova, Ekaterina S.,Stavrianidi, Andrey N.,Rodin, Igor A.,Konevega, Andrey L.,Sergiev, Petr V.,Sumbatyan, Natalia V.,Mankin, Alexander S.,Bogdanov, Alexey A.,Polikanov, Yury S.. "Binding and Action of Amino Acid Analogs of Chloramphenicol upon the Bacterial Ribosome". . p. 842 - 852. Retrieved 2018/02/26.