(1R,4S)-4-((tert-Butoxycarbonyl)amino)cyclopent-2-enecarboxylic acid

Base Information

• Chemical Name: (1R,4S)-4-((tert-Butoxycarbonyl)amino)cyclopent-2-enecarboxylic acid
• CAS No.: 151907-80-1
• Molecular Formula: C11H17NO4
• Molecular Weight: 227.26
• Hs Code.: 29223900
• European Community (EC) Number: 634-894-4
• Nikkaji Number: J2.000.226C
• Wikidata: Q76393722
• Mol file: 151907-80-1.mol

Synonyms:151907-80-1;(1R,4S)-4-((tert-Butoxycarbonyl)amino)cyclopent-2-enecarboxylic acid;108999-93-5;(+)-(1R,4S)-N-BOC-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID;(1R,4S)-4-(tert-butoxycarbonylamino)cyclopent-2-enecarboxylic acid;(1r,4s)-4-{[(tert-butoxy)carbonyl]amino}cyclopent-2-ene-1-carboxylic acid;(1S,4R)-N-BOC-1-Aminocyclopent-2-ene-4-carboxylic acid;(1R,4S)-Boc-4-aminocyclopent-2-ene-carboxylic acid;(1R,4S)-4-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopent-2-ene-1-carboxylic acid;cis-4-((tert-Butoxycarbonyl)amino)cyclopent-2-enecarboxylic acid;(1R,4S)-4-(BOC-amino)cyclopent-2-enecarboxylic acid;(+)-(1S,4R)-N-Boc-1-Aminocyclopent-2-ene-4-carboxy;SCHEMBL605621;WOUNTSATDZJBLP-JGVFFNPUSA-N;cis-4-tert-Butoxycarbonylamino-cyclopent-2-enecarboxylic acid;(1R,4S)-4-((tert-Butoxycarbonyl)amino)cyclopent-2-enecarboxylicacid;(1R,4S)-4-(tert-butoxycarbonylamino)cyclopent-2-ene-1-carboxylic acid;(1R,4S)-4-tert-Butoxycarbonylamino-cyclopent-2-enecarboxylic acid;MFCD00211288;(1R,4S)-4-[(tert-butoxycarbonyl)amino]cyclopent-2-ene-1-carboxylic acid;AKOS015855430;AKOS015915570;CS-W010417;BB 0261607;EN300-6746421;A809235;cis-4-Boc-amino-2-cyclopentene-1-carboxylic acid;cis-4-(tert-Butoxycarbonyl-amino)cyclopent-2-ene-1-carboxylic acid;(1R,4s)-4-(tert-butoxycarbonyl)aminocyclopentane-2-encarboxylic acid;(1R,4S)-4-(tert-Butyloxycarbonylamino)-2-cyclopentene-1-carboxylic acid;(1R,4S)-4-[(tert-butoxycarbonyl)amino]cyclopent-2-ene-1 -carboxylic acid;(1R,4S)-(+)-4-(Boc-amino)-2-cyclopentene-1-carboxylic acid, purum, >=98.0% (HPLC);2-Cyclopentene-1-carboxylicacid,4-[[(1,1-dimethylethoxy)carbonyl]amino]-,(1R,4S)-

Chemical Property of (1R,4S)-4-((tert-Butoxycarbonyl)amino)cyclopent-2-enecarboxylic acid

Chemical Property:

• Appearance/Colour: off-white crystalline powder
• Vapor Pressure: 6.65E-07mmHg at 25°C
• Melting Point: 152 °C
• Refractive Index: 1.514
• Boiling Point: 382.284 °C at 760 mmHg
• PKA: 4.31±0.40(Predicted)
• Flash Point: 184.999 °C
• PSA: 75.63000
• Density: 1.181 g/cm³
• LogP: 1.93130
• Storage Temp.: 2-8°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 227.11575802
• Heavy Atom Count: 16
• Complexity: 316

Purity/Quality:

98%,99%, ^*data from raw suppliers

(+)-(1R,4S)-N-Boc-4-aminocyclopent-2-enecarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1CC(C=C1)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H]1C[C@H](C=C1)C(=O)O

Technology Process of (1R,4S)-4-((tert-Butoxycarbonyl)amino)cyclopent-2-enecarboxylic acid

There total 7 articles about (1R,4S)-4-((tert-Butoxycarbonyl)amino)cyclopent-2-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%

di-tert-butyl dicarbonate (24424-99-5) + (1R,4S)-4-aminocyclopenten-2-ene-1-carboxylic acid (134003-04-6) → (1R,4S)-4-[(tert-butoxycarbonyl)amino]cyclopent-2-ene-1-carboxylic acid (151907-80-1,108999-93-5)

Guidance literature:

di-tert-butyl dicarbonate; (1R,4S)-4-aminocyclopenten-2-ene-1-carboxylic acid; With sodium hydrogencarbonate; In tetrahydrofuran; water;

With hydrogenchloride; In water; at 0 ℃; pH=3; Acidic conditions;

Reference yield: 43.0%

(4S)-N-tert-butoxycarbonyl-4-aminocyclopent-2-ene-1-carboxylic acid methyl ester → (1R,4S)-4-[(tert-butoxycarbonyl)amino]cyclopent-2-ene-1-carboxylic acid (151907-80-1,108999-93-5) + (1S,4S)-N-tert-butoxycarbonyl-4-aminocyclopent-2-ene-1-carboxylic acid methyl ester + (1S,4S)-N-tert-butoxycarbonyl-4-aminocyclopent-2-ene-1-carboxylic acid (108999-93-5)

Guidance literature:

With lipase type VII from Candida rugosa; In phosphate buffer; at 26 ℃; for 24h; pH=7;

DOI:10.1016/j.tet.2003.10.116

Reference yield:

(-)-[(1R,4S)-tert-butyl 3-oxo-2-azabicyclo(2.2.1)hept-5-ene-2-carboxylate] (200002-41-1) → C11H17NO4 (1312161-66-2) + (1R,4S)-4-[(tert-butoxycarbonyl)amino]cyclopent-2-ene-1-carboxylic acid (151907-80-1,108999-93-5) + (1S,4S)-N-tert-butoxycarbonyl-4-aminocyclopent-2-ene-1-carboxylic acid (108999-93-5)

Guidance literature:

(-)-[(1R,4S)-tert-butyl 3-oxo-2-azabicyclo(2.2.1)hept-5-ene-2-carboxylate]; With sodium methylate; In methanol; at 2 ℃; for 5h;

With acetic acid; at 2 - 10 ℃; pH=6;

With lithium hydrochloride monohydrate; water; In methanol; at -3.5 - 2 ℃; for 92.5h; Inert atmosphere;

upstream raw materials:

di-tert-butyl dicarbonate

(1R,4S)-4-aminocyclopenten-2-ene-1-carboxylic acid

(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

2-azabicyclo[2.2.1.]hept-5-en-3-one

Downstream raw materials:

(1R,4S)-N-tert-butoxycarbonyl-4-aminocyclopent-2-ene-1-carboxylic acid methyl ester

(1S,cis)-tert-butyl N-[4-(hydroxymethyl)-2-cyclopenten-1-yl]carbamate

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride

(1S,4R)-1-amino-4-benzyloxycarbonyl-cyclopent-2-ene hydrochloride

Refernces

• 1、 -. "AMINOCYCLOPENTYL PYRIDOPYRAZINONE MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY". Page/Page column 27. . Retrieved 2010/11/27.
• 2、 -. "TETRAHYDROPYRANYL CYCLOPENTYL 1-SUBSTITUTED AND 1,1-DISUBSTITUTED TETRAHYDROISOQUINOLINE MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY". Page/Page column 30. . Retrieved 2010/02/14.