(R)-4-N-Cbz-piperazine-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (R)-4-N-Cbz-piperazine-2-carboxylic acid methyl ester
• CAS No.: 405175-79-3
• Molecular Formula: C14H18N2O4
• Molecular Weight: 278.308
• DSSTox Substance ID: DTXSID70426859
• Wikidata: Q72500050
• Mol file: 405175-79-3.mol

Synonyms:405175-79-3;(R)-4-N-Cbz-piperazine-2-carboxylic acid methyl ester;(r)-1-benzyl 3-methyl piperazine-1,3-dicarboxylate;1-O-benzyl 3-O-methyl (3R)-piperazine-1,3-dicarboxylate;MFCD04115337;(R)-Piperazine-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester;1-benzyl 3-methyl (R)-piperazine-1,3-dicarboxylate;(R)-1-Benzyl-3-methyl piperazine-1,3-dicarboxylate;(R)-4-N-Cbz-piperazine-2-carboxylic acid methylester;(R)-4-N-Cbz-piperazine-3-carboxylic acid methylester;SCHEMBL12324603;DTXSID70426859;AKOS005259477;AKOS015897819;AS-38715;CS-0200100;(r)-1-benzyl3-methylpiperazine-1,3-dicarboxylate;benzyl (R)-3-carbomethoxypiperazine-1-carboxylate;Q-102955;1-BENZYL 3-METHYL (3R)-PIPERAZINE-1,3-DICARBOXYLATE

Chemical Property of (R)-4-N-Cbz-piperazine-2-carboxylic acid methyl ester

Chemical Property:

• Vapor Pressure: 8.08E-07mmHg at 25°C
• Boiling Point: 406.5°C at 760 mmHg
• Flash Point: 199.7°C
• PSA: 67.87000
• Density: 1.212
• LogP: 1.03670
• Storage Temp.: 2-8°C
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 278.12665706
• Heavy Atom Count: 20
• Complexity: 342

Purity/Quality:

98%min ^*data from raw suppliers

(R)-1-Benzyl3-methylpiperazine-1,3-dicarboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CN(CCN1)C(=O)OCC2=CC=CC=C2
• Isomeric SMILES: COC(=O)[C@H]1CN(CCN1)C(=O)OCC2=CC=CC=C2

Technology Process of (R)-4-N-Cbz-piperazine-2-carboxylic acid methyl ester

There total 7 articles about (R)-4-N-Cbz-piperazine-2-carboxylic acid methyl 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: 55.0%

→ 1-benzyl 3-methyl (3S)-piperazine-1,3-dicarboxylate (225517-81-7) + 1-benzyl 3-methyl (3R)-4-(3-mesitylpropanoyl)piperazine-1,3-dicarboxylate (1394957-81-3) + 1-benzyl 3-methyl (3S)-4-(3-mesitylpropanoyl)piperazine-1,3-dicarboxylate + (R)-4-((benzyloxy)carbonyl)piperazine-2-carboxylic acid (405175-79-3)

Guidance literature:

With 2-(2,4,6-trimethyl-phenyl)-2,5,6,7-tetrahydro-pyrrolo[2,1-c] [1,2,4]triazol-4-ylium perchlorate; (4aR,9aS)-6-bromo-4-hydroxy-4,4a,9,9a-tetrahydroindeno[2,1-b][1,4]oxazin-3(2H)-one; potassium carbonate; In Isopropyl acetate; at 23 ℃; for 24h;

Reference yield:

methanol (67-56-1) + (2R)-4-[(benzyloxy)carbonyl]-1-[(tert-butoxy)carbonyl]piperazine-2-carboxylic acid (138775-02-7) → (R)-4-((benzyloxy)carbonyl)piperazine-2-carboxylic acid (405175-79-3)

Guidance literature:

With acetyl chloride; for 3.33333h; Reflux;

DOI:10.1016/j.bmcl.2021.128499

Reference yield:

(R)-5-Oxo-piperazine-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester → (R)-4-((benzyloxy)carbonyl)piperazine-2-carboxylic acid (405175-79-3)

Guidance literature:

With borane; In tetrahydrofuran;

DOI:10.1021/jm990418b

upstream raw materials:

3-amino-N-[(benzyloxy)carbonyl]-D-alanine methyl ester

benzyl chloroformate

Methyl (R)-6-oxopiperazine-2-carboxylate

1-benzyl 3-methyl piperazine-1,3-dicarboxylate

Downstream raw materials:

benzyl (3R)-3-[(acetyloxy)methyl]-4-{[1-(3-ethoxyphenyl)-2-(4-methylphenyl)-1H-imidazol-4-yl]carbonyl}piperazine-1-carboxylate

benzyl (3R)-4-{[1-(3-ethoxyphenyl)-2-(4-methylphenyl)-1H-imidazol-4-yl]carbonyl}-3-(hydroxymethyl)-piperazine-1-carboxylate

((2R)-1-{[1-(3-ethoxyphenyl)-2-(4-methylphenyl)-1H-imidazol-4-yl]carbonyl}piperazin-2-yl)methyl acetate

methyl 3-[(3R)-4-{[1-(3-ethoxyphenyl)-2-(4-methylphenyl)-1H-imidazol-4-yl]carbonyl}-3-(hydroxymethyl)piperazin-1-yl]-1-naphthoate

Refernces

• 1、 -. "KINETIC RESOLUTION OF CHIRAL AMINES". Page/Page column 69; 70; 71; 78; 79; 80. . Retrieved 2013/03/26.
• 2、 Hoekstra, William J.,Maryanoff, Bruce E.,Damiano, Bruce P.,Andrade-Gordon, Patricia,Cohen, Judith H.,Costanzo, Michael J.,Haertlein, Barbara J.,Hecker, Leonard R.,Hulshizer, Becky L.,Kauffman, Jack A.,Keane, Patricia,McComsey, David F.,Mitchell, John A.,Scott, Lorraine,Shah, Rekha D.,Yabut, Stephen C.. "Potent, orally active GPIIb/IIIa antagonists containing a nipecotic acid subunit. Structure-activity studies leading to the discovery of RWJ-53308". . p. 5254 - 5265. Retrieved 2007/10/03.