N-Tert-boc-L-isoleucine N-succinimide ester

Base Information

• Chemical Name: N-Tert-boc-L-isoleucine N-succinimide ester
• 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:3392-08-3;N-TERT-BOC-L-ISOLEUCINE N-SUCCINIMIDE ESTER;(2,5-Dioxopyrrolidin-1-yl) (2S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate;AKOS016003057;CS-W011975;DS-16130

Chemical Property of N-Tert-boc-L-isoleucine N-succinimide ester

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
• Isomeric SMILES: CCC(C)[C@@H](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 N-Tert-boc-L-isoleucine N-succinimide ester

There total 7 articles about N-Tert-boc-L-isoleucine N-succinimide ester 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:

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

Boc-Ile-Gly-OPac

(S)-isoleucine benzyl amide

{(1S,2S,4R)-1-Benzyl-4-[(S)-1-(2,3-dihydroxy-propylcarbamoyl)-2-methyl-butylcarbamoyl]-2-hydroxy-5-phenyl-pentyl}-carbamic acid tert-butyl ester