4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid

Base Information

• Chemical Name: 4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid
• CAS No.: 149057-19-2
• Molecular Formula: C18H24N2O6
• Molecular Weight: 364.398
• Hs Code.: 2933599090
• European Community (EC) Number: 672-409-8
• DSSTox Substance ID: DTXSID10933537
• Mol file: 149057-19-2.mol

Synonyms:149057-19-2;N-1-Boc-N-4-Cbz-2-piperazine carboxylic acid;4-((benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid;1-[(2-methylpropan-2-yl)oxycarbonyl]-4-phenylmethoxycarbonylpiperazine-2-carboxylic acid;4-[(benzyloxy)carbonyl]-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid;4-CBZ-1-Boc-piperazine-2-carboxylic acid;MFCD02683055;1-Boc-4-Cbz-2-piperazinecarboxylic Acid;4-[(Benzyloxy)carbonyl]-1-(tert-butoxycarbonyl)-piperazine-2-carboxylic acid;1-N-BOC-4-N-CBZ-PIPERAZINE-2-CARBOXYLIC ACID;4-[(benzyloxy)carbonyl]-1-[(tert-butoxy)carbonyl]piperazine-2-carboxylic acid;Piperazine-1,2,4-tricarboxylic acid 4-benzyl ester 1-tert-butyl ester;MFCD02179112;4-(benzyloxycarbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid;SCHEMBL957813;DTXSID10933537;(2R)-1-phenylmethoxycarbonyl-4-tert-butoxycarbonyl-piperazine-2-carboxylate;AKOS005264454;AB11012;AB11016;1-Boc-4-Cbz-piperazine-2-carboxylicacid;AC-14344;AM803242;BP-11531;DS-13925;SY020410;SY039724;A2695;CS-0035765;FT-0643108;FT-0643296;FT-0650092;FT-0773392;N1-Boc-N-4-Cbz-piperazine-2-carboxylic acid;(r)-1-boc-4-cbz-piperazine-2-carboxylic acid;EN300-7366482;(S)-N-1-Boc-N-4-Cbz-2-piperazinecarboxylic acid;Q-102277;1-tert-butoxycarbonyl-4-benzyloxycarbonylpiperazine-2-ylcarboxylic acid;4-((benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylicacid;4-[(Benzyloxy)carbonyl]-1-(tert-butoxycarbonyl)-2-piperazinecarboxylic acid

Chemical Property of 4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid

Chemical Property:

• Refractive Index: 1.555
• Boiling Point: 518.912 °C at 760 mmHg
• PKA: 3.69±0.20(Predicted)
• Flash Point: 267.629 °C
• PSA: 96.38000
• Density: 1.273 g/cm³
• LogP: 2.20490
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 364.16343649
• Heavy Atom Count: 26
• Complexity: 524

Purity/Quality:

99% ^*data from raw suppliers

4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCN(CC1C(=O)O)C(=O)OCC2=CC=CC=C2
• Uses: 4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid is a useful intermediate used in the preparation of N-aryl piperazines as new CXCR4 antagonists and antivirals.

Technology Process of 4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid

There total 8 articles about 4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid 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: 80.0%

piperazine-2-carboxylic acid (2762-32-5) + N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) + 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile (58632-95-4) → 4-((benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid (149057-19-2)

Guidance literature:

piperazine-2-carboxylic acid; N-(Benzyloxycarbonyloxy)succinimide; With sodium hydroxide; In 1,4-dioxane; water; at 20 ℃; for 0.75h; pH=9.5 - 11;

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile; In 1,4-dioxane; water; at 20 ℃; for 17h; pH=9.5;

With hydrogenchloride; In 1,4-dioxane; water; pH=2;

Reference yield: 69.0%

1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid (1214196-85-6) + benzyl chloroformate (501-53-1,94274-21-2) → 4-((benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid (149057-19-2)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; at 25 ℃; for 4h;

Reference yield: 48.0%

di-tert-butyl dicarbonate (24424-99-5) + 4-(benzyloxy-carbonyl)-2-piperazinecarboxylic acid (934630-06-5,64172-98-1) → 4-((benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid (149057-19-2)

Guidance literature:

4-(benzyloxy-carbonyl)-2-piperazinecarboxylic acid; With sodium hydrogencarbonate; In 1,4-dioxane; water; at 20 ℃; for 0.5h;

di-tert-butyl dicarbonate; In 1,4-dioxane; water; at 0 - 20 ℃;

upstream raw materials:

4-benzyl 1-(tert-butyl) 2-methyl piperazine-1,2,4-tricarboxylate

di-tert-butyl dicarbonate

4-(benzyloxy-carbonyl)-2-piperazinecarboxylic acid

piperazine-2-carboxylic acid

Downstream raw materials:

4-benzyl 1-(tert-butyl) 2-carbamoylpiperazine-1,4-dicarboxylate

4-benzyl 1-tert-butyl 2-(methylcarbamoyl)piperazine-1,4-dicarboxylate

C₂₉H₃₀F₃N₃O₆S

C₂₇H₂₆F₃N₃O₆S

Refernces

• 1、 -. "HEPATITIS B CAPSID ASSEMBLY MODULATORS". Paragraph 0416; 0417. . Retrieved 2019/12/30.
• 2、 Gentles, Robert G.,Ding, Min,Zheng, Xiaofan,Chupak, Louis,Poss, Michael A.,Beno, Brett R.,Pelosi, Lenore,Liu, Mengping,Lemm, Julie,Wang, Ying-Kai,Roberts, Susan,Gao, Min,Kadow, John. "SAR studies on a series of N-benzyl-4-heteroaryl-1-(phenylsulfonyl) piperazine-2-carboxamides: Potent inhibitors of the polymerase enzyme (NS5B) of the hepatitis C virus". scheme or table. p. 3142 - 3147. Retrieved 2011/06/24.