N-(Benzyloxycarbonyl)-L-aspartic acid diethyl ester

Base Information

• Chemical Name: N-(Benzyloxycarbonyl)-L-aspartic acid diethyl ester
• CAS No.: 57471-70-2
• Molecular Formula: C₁₆H₂₁NO₆
• Molecular Weight: 323.346
• DSSTox Substance ID: DTXSID001222241
• Nikkaji Number: J984.334E
• Mol file: 57471-70-2.mol

Synonyms:DTXSID001222241;N-(Benzyloxycarbonyl)-L-aspartic acid diethyl ester;1,4-Diethyl N-[(phenylmethoxy)carbonyl]-L-aspartate;57471-70-2

Chemical Property of N-(Benzyloxycarbonyl)-L-aspartic acid diethyl ester

Chemical Property:

• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 11
• Exact Mass: 323.13688739
• Heavy Atom Count: 23
• Complexity: 392

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CC(C(=O)OCC)NC(=O)OCC1=CC=CC=C1
• Isomeric SMILES: CCOC(=O)C[C@@H](C(=O)OCC)NC(=O)OCC1=CC=CC=C1

Technology Process of N-(Benzyloxycarbonyl)-L-aspartic acid diethyl ester

There total 4 articles about N-(Benzyloxycarbonyl)-L-aspartic acid diethyl 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%

ethanol (64-17-5) + N-Benzyloxycarbonyl-L-asparaginsaeure-β-aethylester (39256-89-8) → diethyl N-benzyloxycarbonyl-(S)-aspartate (57471-70-2)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; at 0 - 20 ℃; for 1h;

DOI:10.1016/j.bmcl.2021.128267

Reference yield:

L-aspartic acid diethyl ester (13552-87-9) + benzyl chloroformate (501-53-1,94274-21-2) → diethyl N-benzyloxycarbonyl-(S)-aspartate (57471-70-2)

Guidance literature:

With sodium hydrogencarbonate;

DOI:10.1248/cpb.33.3299

Reference yield:

diethyl L-aspartate hydrochloride (16115-68-7) + benzyl chloroformate (501-53-1,94274-21-2) → diethyl N-benzyloxycarbonyl-(S)-aspartate (57471-70-2)

Guidance literature:

With sodium hydrogencarbonate; Inert atmosphere;

DOI:10.1039/c4cc01692k

upstream raw materials:

L-aspartic acid diethyl ester

benzyl chloroformate

diethyl L-aspartate hydrochloride

ethanol

Downstream raw materials:

[(1S)-3-hydroxy-1-(hydroxymethyl)propyl]carbamic acid phenylmethyl ester

2-[(4S)-(3-benzyloxycarbonyl-2,2-dimethyl-1,3-oxazolidin-4-y)]ethanol

C₃₅H₄₅N₃O₈S₂

C₃₅H₄₅N₃O₈S₂

Refernces

• 1、 Garner, Philip,Weerasinghe, Laksiri,Van Houten, Ian,Hu, Jieyu. "A concise [C+NC+CC] coupling-enabled synthesis of kaitocephalin". . p. 4908 - 4910. Retrieved 2014/05/06.
• 2、 Ikota,Shibata,Koga. "Stereoselective reactions. IX. Synthetic studies on optically active β-lactams. I. Chiral synthesis of carbapenam and carbapenem ring systems starting from (S)-aspartic acid". . p. 3299 - 3306. Retrieved 2007/10/02.