(S)-dimethyl 2-benzamidopentanedioate

Base Information

• Chemical Name: (S)-dimethyl 2-benzamidopentanedioate
• CAS No.: 86555-46-6
• Molecular Formula: C14H17NO5
• Molecular Weight: 279.293
• DSSTox Substance ID: DTXSID00427536
• Nikkaji Number: J2.619.949B
• Wikidata: Q82240190
• Mol file: 86555-46-6.mol

Synonyms:(S)-dimethyl 2-benzamidopentanedioate;86555-46-6;dimethyl benzoyl-L-glutamate;dimethyl (2S)-2-benzamidopentanedioate;(S)-Dimethyl2-benzamidopentanedioate;dimethyl N-benzoyl-(s)-glutamate;DTXSID00427536;AKOS016844378;CS-0361298;1,5-dimethyl 2-(phenylformamido)pentanedioate;A850030;J-502487;(S)-2-(Benzoylamino)pentanedioic acid dimethyl ester;1,5-DIMETHYL (2S)-2-(PHENYLFORMAMIDO)PENTANEDIOATE

Chemical Property of (S)-dimethyl 2-benzamidopentanedioate

Chemical Property:

• PSA: 85.19000
• LogP: 1.48600
• Storage Temp.: 2-8°C
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 279.11067264
• Heavy Atom Count: 20
• Complexity: 350

Purity/Quality:

99% ^*data from raw suppliers

(S)-Dimethyl2-benzamidopentanedioate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CCC(C(=O)OC)NC(=O)C1=CC=CC=C1
• Isomeric SMILES: COC(=O)CC[C@@H](C(=O)OC)NC(=O)C1=CC=CC=C1

Technology Process of (S)-dimethyl 2-benzamidopentanedioate

There total 10 articles about (S)-dimethyl 2-benzamidopentanedioate 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: 93.0%

dimethyl (2S)-2-(N-benzoyl-N-tert-butoxycarbonyl)aminopentanedioate (863764-30-1) → dimethyl (2S)-2-benzoylaminopentanedioate (86555-46-6,1346808-85-2,1346773-61-2)

Guidance literature:

With montmorillonite K-10; In toluene; at 65 ℃; for 3h;

DOI:10.1002/ejoc.200700296

Reference yield: 92.0%

dimethyl glutamate hydrochloride (23150-65-4,27025-25-8,13515-99-6) + benzoyl chloride (98-88-4) → dimethyl N-benzoyl-(RS)-glutamate (86555-46-6,1346808-85-2,1346773-61-2)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 2h;

DOI:10.1134/S1070428017050190

Reference yield: 91.0%

L-glutamic dimethyl ester hydrochloride (23150-65-4) + benzoyl chloride (98-88-4) → dimethyl (2S)-2-benzoylaminopentanedioate (86555-46-6,1346808-85-2,1346773-61-2)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 2h;

DOI:10.1134/S1070428017050190

upstream raw materials:

Glutamic acid

dimethyl glutamate hydrochloride

benzoyl chloride

L-glutamic acid dimethyl ester

Downstream raw materials:

dimethyl (2S)-2-(N-benzoyl-N-tert-butoxycarbonyl)aminopentanedioate

N-benzoyl-L-glutamic acid dihydrazide

(1S)-N-[4-hydroxy-1-(hydroxymethyl)butyl]benzamide

N-benzoyl-L-glutamic acid α-methyl ester

Refernces

• 1、 Thangavelu, Bharani,Mutthamsetty, Vinay,Wang, Qinzhe,Viola, Ronald E.. "Design and optimization of aspartate N-acetyltransferase inhibitors for the potential treatment of Canavan disease". . p. 870 - 885. Retrieved 2017/02/05.
• 2、 Avent, Anthony G.,Duggan, Heather M. E.,Young, Douglas W.. "Synthesis of protected γ-carboxyglutamates and γ-acylglutamates by rearrangement of N,N-diacylglutamates". . p. 2327 - 2332. Retrieved 2007/10/03.