Ethyl 2-(((benzyloxy)carbonyl)amino)-2-cyanoacetate

Base Information

• Chemical Name: Ethyl 2-(((benzyloxy)carbonyl)amino)-2-cyanoacetate
• CAS No.: 3878-13-5
• Molecular Formula: C₁₃H₁₄N₂O₄
• Molecular Weight: 262.265
• DSSTox Substance ID: DTXSID30433160
• Nikkaji Number: J2.329.786H
• Mol file: 3878-13-5.mol

Synonyms:3878-13-5;Ethyl 2-(((benzyloxy)carbonyl)amino)-2-cyanoacetate;ETHYL 2-(BENZYLOXYCARBONYLAMINO)-2-CYANOACETATE;ethyl 2-benzyloxycarbonylamino-2-cyanoacetate;ethyl 2-cyano-2-(phenylmethoxycarbonylamino)acetate;ETHYL N-(BENZYLOXYCARBONYL)-AMINOCYANOACETATE;ethyl2-(benzyloxycarbonylamino)-2-cyanoacetate;Glycine,N-carboxy-2-cyano-,N-benzyl ethyl ester;ETHYL 2-{[(BENZYLOXY)CARBONYL]AMINO}-2-CYANOACETATE;SCHEMBL498359;2-benzyloxycarbonylamino-2-cyanoacetic acid ethyl ester;AMY4845;DTXSID30433160;BGDPLMKKSXSSTM-UHFFFAOYSA-N;CS-B1227;AKOS027390961;D77281;EN300-7390359;Ethyl N-[(benzyloxy)carbonyl]-3-nitriloalaninate;Ethyl2-(((benzyloxy)carbonyl)amino)-2-cyanoacetate;2-[(Benzyloxycarbonyl)amino]-2-cyanoacetic acid ethyl ester

Chemical Property of Ethyl 2-(((benzyloxy)carbonyl)amino)-2-cyanoacetate

Chemical Property:

• PSA: 88.42000
• LogP: 1.75898
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 262.09535693
• Heavy Atom Count: 19
• Complexity: 355

Purity/Quality:

99%, ^*data from raw suppliers

Ethyl2-(((benzyloxy)carbonyl)amino)-2-cyanoacetate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(C#N)NC(=O)OCC1=CC=CC=C1

Technology Process of Ethyl 2-(((benzyloxy)carbonyl)amino)-2-cyanoacetate

There total 6 articles about Ethyl 2-(((benzyloxy)carbonyl)amino)-2-cyanoacetate 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: 70.0%

dioxane-water (56955-16-9) + benzyl chloroformate (501-53-1,94274-21-2) + ethyl-2-aminocyano acetate (32683-02-6) → (RS)-ethyl 2-(benzyloxycarbonylamino)-2-cyanoacetate (147194-08-9,3878-13-5)

Guidance literature:

Reference yield: 64.2%

benzyl chloroformate (501-53-1,94274-21-2) + ethyl cyanoglyoxylate-2-oxime (3849-21-6) → (RS)-ethyl 2-(benzyloxycarbonylamino)-2-cyanoacetate (147194-08-9,3878-13-5)

Guidance literature:

With sodium hydrogencarbonate; sodium hydrogensulfite; In water; at 0 - 30 ℃; for 4h;

Reference yield: 60.2%

benzyl chloroformate (501-53-1,94274-21-2) + ethyl-2-aminocyano acetate (32683-02-6) → (RS)-ethyl 2-(benzyloxycarbonylamino)-2-cyanoacetate (147194-08-9,3878-13-5)

Guidance literature:

With pyridine; In water;

upstream raw materials:

benzyl chloroformate

ethyl-2-aminocyano acetate

dioxane-water

ethyl cyanoglyoxylate-2-oxime

Downstream raw materials:

(2S,3S,5R)-1-benzyl 2-ethyl-2-cyano-5-hydroxy-3-phenylpyrrolidine-1,2-dicarboxylate

(2R,3S,5R)-1-benzyl 2-ethyl-2-cyano-5-hydroxy-3-phenylpyrrolidine-1,2-dicarboxylate

(RS)-N-benzyl 2-(benzyloxycarbonylamino)-2-(thiazol-2-yl)acetamide

(RS)-N-benzyl 2-(benzyloxycarbonyl)amino-2-thiocarbamoylacetamide

Refernces

• 1、 Baruah, Pranjal K.,Dinsmore, Jason,King, Amber M.,Salomé, Christophe,De Ryck, Marc,Kaminski, Rafal,Provins, Laurent,Kohn, Harold. "Synthesis, anticonvulsant activity, and neuropathic pain-attenuating activity of N-benzyl 2-amino-2-(hetero)aromatic acetamides". supporting information; experimental part. p. 3551 - 3564. Retrieved 2012/07/28.
• 2、 -. "SUCCINIC ACID DIESTER DERIVATIVE, PROCESS FOR PRODUCTION THEREOF, AND USE OF THE DERIVATIVE IN THE PRODUCTION OF PHARMACEUTICAL PREPARATION". Page/Page column 7. . Retrieved 2009/06/27.