Isoleucine, N-((2-chloroethyl)nitrosocarbamoyl)-, L-

Base Information

• Chemical Name: Isoleucine, N-((2-chloroethyl)nitrosocarbamoyl)-, L-
• CAS No.: 80687-30-5
• Molecular Formula: C₉H₁₆ClN₃O₄
• Molecular Weight: 265.697
• DSSTox Substance ID: DTXSID00230502
• Wikidata: Q76156415
• Mol file: 80687-30-5.mol

Synonyms:BRN 5562830;Isoleucine, N-((2-chloroethyl)nitrosocarbamoyl)-, L-;80687-30-5;N-((2-Chloroethyl)nitrosocarbamoyl)-L-isoleucine;L-Isoleucine, N-(((2-chloroethyl)nitrosoamino)carbonyl)-;N-(Chloro-2 ethyl)-N-nitrosocarbamyl-L-isoleucine [French];N-(Chloro-2 ethyl)-N-nitrosocarbamyl-L-isoleucine;DTXSID00230502;LS-84765

Chemical Property of Isoleucine, N-((2-chloroethyl)nitrosocarbamoyl)-, L-

Chemical Property:

• Density: 1.36g/cm³
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 265.0829337
• Heavy Atom Count: 17
• Complexity: 287

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)C(C(=O)O)NC(=O)N(CCCl)N=O
• Isomeric SMILES: CC[C@H](C)[C@@H](C(=O)O)NC(=O)N(CCCl)N=O

Technology Process of Isoleucine, N-((2-chloroethyl)nitrosocarbamoyl)-, L-

There total 4 articles about Isoleucine, N-((2-chloroethyl)nitrosocarbamoyl)-, L- 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: 77.0%

ester benzylique de la N-(chloro-2-ethyl)-N-nitrosocarbamyl-L-isoleucine (96409-00-6) → N--L-isoleucine (80687-30-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; cyclohexene; for 1h; Heating;

Reference yield:

L-isoleucine benzyl ester tosylate (16652-75-8) → N--L-isoleucine (80687-30-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / triethylamine / dimethylformamide / 5 h / 0 °C

2: 77 percent / hydrogen / 10percent Pd/C / ethanol; cyclohexene / 1 h / Heating

With hydrogen; triethylamine; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide; cyclohexene;

Reference yield:

(2S,3S)-2-[3-(2-Chloro-ethyl)-ureido]-3-methyl-pentanoic acid → N--L-isoleucine (80687-30-5)

Guidance literature:

With hydrogenchloride; sodium nitrite; In diethyl ether; at 5 ℃; for 0.5h; Yield given;

DOI:10.1002/ardp.19843170602

upstream raw materials:

ester benzylique de la N-(chloro-2-ethyl)-N-nitrosocarbamyl-L-isoleucine

L-isoleucine

L-isoleucine benzyl ester tosylate

Downstream raw materials:

C₁₅H₂₁ClN₄O₃

Refernces

• 1、 Ehresmann,Zelezny,Eisenbrand. "Syntheses of potentially antineoplastic amides and esters of N-[N'-2(2-chloroethyl)-N'-nitrosocarbamoyl]amino acids, II". . p. 481 - 487. Retrieved 2007/10/02.