1-((tert-Butoxycarbonyl)amino)cyclopent-3-enecarboxylic acid

Base Information

• Chemical Name: 1-((tert-Butoxycarbonyl)amino)cyclopent-3-enecarboxylic acid
• CAS No.: 213316-20-2
• Molecular Formula: C11H17NO4
• Molecular Weight: 227.26
• Hs Code.: 2924299090
• European Community (EC) Number: 890-111-8
• DSSTox Substance ID: DTXSID90442117
• Nikkaji Number: J2.503.418J
• Mol file: 213316-20-2.mol

Synonyms:213316-20-2;1-((tert-Butoxycarbonyl)amino)cyclopent-3-enecarboxylic acid;1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopent-3-ene-1-carboxylic Acid;1-TERT-BUTOXYCARBONYLAMINO-CYCLOPENT-3-ENECARBOXYLIC ACID;1-(TERT-BUTOXYCARBONYLAMINO)CYCLOPENT-3-ENECARBOXYLIC ACID;1-(BOC-amino)cyclopent-3-enecarboxylic acid;SCHEMBL1157610;1-((tert-Butoxycarbonyl)amino)cyclopent-3-enecarboxylicacid;DTXSID90442117;XAUHKCBBMAAOMD-UHFFFAOYSA-N;AMY25985;MFCD02683161;AKOS016009666;AB12420;AS-41331;CS-0186208;EN300-313322;A850301;Z1505697251;1-(tert-Butyloxycarbonylamino)-3-cyclopentene-1-carboxylic acid;1-((Tert-butoxycarbonyl)amino)cyclopent-3-enecarboxylic acid, 98%;1-{[(tert-butoxy)carbonyl]amino}cyclopent-3-ene-1-carboxylic acid;1-[(TERT-BUTOXYCARBONYL)AMINO]CYCLOPENT-3-ENE-1-CARBOXYLIC ACID

Chemical Property of 1-((tert-Butoxycarbonyl)amino)cyclopent-3-enecarboxylic acid

Chemical Property:

• Melting Point: 137 °C
• Boiling Point: 380.9±41.0 °C(Predicted)
• PKA: 3.89±0.20(Predicted)
• PSA: 79.12000
• Density: 1.18±0.1 g/cm3(Predicted)
• LogP: 1.88890
• Storage Temp.: 2-8°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 227.11575802
• Heavy Atom Count: 16
• Complexity: 319

Purity/Quality:

99% ^*data from raw suppliers

1-((tert-Butoxycarbonyl)amino)cyclopent-3-enecarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1(CC=CC1)C(=O)O

Technology Process of 1-((tert-Butoxycarbonyl)amino)cyclopent-3-enecarboxylic acid

There total 7 articles about 1-((tert-Butoxycarbonyl)amino)cyclopent-3-enecarboxylic 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: 100.0%

1-tert-butoxycarbonylamino-cyclopent-3-enecarboxylic acid methyl ester (288303-88-8) → 1-(tert-butoxycarbonylamino)-3-cyclopentene-1-carboxylic acid (213316-20-2)

Guidance literature:

With water; sodium hydroxide; In methanol;

DOI:10.2533/chimia.2018.848

Reference yield: 87.0%

ethyl 1-((tert-butoxycarbonyl)amino)cyclopent-3-ene-1-carboxylate (207729-00-8) → 1-(tert-butoxycarbonylamino)-3-cyclopentene-1-carboxylic acid (213316-20-2)

Guidance literature:

With sodium hydroxide; In ethanol; water; Heating;

DOI:10.1021/jo9807161

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 1-(tert-butoxycarbonylamino)-3-cyclopentene-1-carboxylic acid (213316-20-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 0.56 g / tetrahydrofuran / 20 h / Heating

2: 80 percent / lithium hydroxide / tetrahydrofuran; H₂O / 0.33 h / 60 °C / microwave irradiation

With lithium hydroxide; In tetrahydrofuran; water;

DOI:10.1016/j.tet.2007.06.108

upstream raw materials:

ethyl 1-((tert-butoxycarbonyl)amino)cyclopent-3-ene-1-carboxylate

C₁₅H₂₄N₂O₂

(2R)-5,5-diallyl-3,6-diethoxy-2,5-dihydro-2-isopropylpyrazine

di-tert-butyl dicarbonate

Downstream raw materials:

1-(tert-butoxycarbonylamino)-cyclopent-3-ene-1-carboxylic acid N-[3-methyl-4-(3-oxo-morpholin-4-yl)-phenyl]-amide

[1-(2'-tert-butylsulfamoyl-3-fluoro-biphenyl-4-ylcarbamoyl)-cyclopent-3-enyl]-carbamic acid tert-butyl ester

Refernces

• 1、 Jam, Fariba,Tullberg, Marcus,Luthman, Kristina,Gr?tli, Morten. "Microwave assisted synthesis of spiro-2,5-diketopiperazines". . p. 9881 - 9889. Retrieved 2008/02/11.
• 2、 Park, Kyung-Ho,Olmstead, Marilyn M.,Kurth, Mark J.. "Diastereoselective Solid-Phase Synthesis of Novel Hydantoin- and Isoxazoline-Containing Heterocycles". . p. 6579 - 6585. Retrieved 2007/10/03.