(-)-(1S,4R)-N-Boc-4-aminocyclopent-2-enecarboxylic acid

Base Information

• Chemical Name: (-)-(1S,4R)-N-Boc-4-aminocyclopent-2-enecarboxylic acid
• CAS No.: 151907-79-8
• Molecular Formula: C₁₁H₁₇NO₄
• Molecular Weight: 227.26
• Hs Code.: 29223900
• European Community (EC) Number: 634-898-6
• Nikkaji Number: J2.654.330D
• Mol file: 151907-79-8.mol

Synonyms:151907-79-8;(-)-(1S,4R)-N-BOC-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID;(1S,4R)-4-((tert-Butoxycarbonyl)amino)cyclopent-2-enecarboxylic acid;(1S,4R)-4-(tert-butoxycarbonylamino)cyclopent-2-enecarboxylic acid;(1S,4R)-4-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopent-2-ene-1-carboxylic acid;(1S,4R)-4-((tert-butoxycarbonyl)amino)cyclopent-2-ene-1-carboxylic acid;(1s,4r)-4-{[(tert-butoxy)carbonyl]amino}cyclopent-2-ene-1-carboxylic acid;108999-93-5;(1R,4S)-N-Boc-1-aminocyclopent-2-ene-4-carboxylic acid;(1S,4R)-4-(BOC-AMINO)CYCLOPENT-2-ENECARBOXYLIC ACID;MFCD00211287;SCHEMBL605147;(1S,4R)-4-tert-Butoxycarbonylamino-cyclopent-2-enecarboxylic acid;cis-4-((tert-Butoxycarbonyl)amino)cyclopent-2-enecarboxylic acid;AMY18729;AKOS015841319;AC-7958;CS-W010416;EN300-6745728;(1s,4r)-4-(BOC-amino)cyclopentene-2-carboxylic acid;(1S,4R)-Boc-4-aminocyclopent-2-ene-carboxylic acid;(1S,4R)-4-((tert-Butoxycarbonyl)amino)cyclopent-2-enecarboxylicacid;(1S)-4alpha-(tert-Butoxycarbonylamino)-2-cyclopentene-1alpha-carboxylic acid;(1S,4R)-(-)-4-(Boc-amino)-2-cyclopentene-1-carboxylic acid, >=98.0% (HPLC);Racemic cis-4-[[(1,1-Dimethylethoxy)carbonyl]amino]-2-cyclopentene-1-carboxylic acid

Chemical Property of (-)-(1S,4R)-N-Boc-4-aminocyclopent-2-enecarboxylic acid

Chemical Property:

• Appearance/Colour: beige to light brown crystalline powder
• Vapor Pressure: 6.65E-07mmHg at 25°C
• Melting Point: 152.9 °C
• Refractive Index: 1.514
• Boiling Point: 382.3 °C at 760 mmHg
• PKA: 4.31±0.40(Predicted)
• Flash Point: 185 °C
• PSA: 75.63000
• Density: 1.18g/cm³
• LogP: 1.93130
• Storage Temp.: under inert gas (nitrogen or Argon) at 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% ^*data from raw suppliers

(-)-(1S,4R)-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

Total 1 MSDS from other Authors

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 (-)-(1S,4R)-N-Boc-4-aminocyclopent-2-enecarboxylic acid

There total 16 articles about (-)-(1S,4R)-N-Boc-4-aminocyclopent-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: 44.0%

(±)-tert-butyl 3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate → (-)-[(1R,4S)-tert-butyl 3-oxo-2-azabicyclo(2.2.1)hept-5-ene-2-carboxylate] (200002-41-1) + (1S-cis)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-2-cyclopentene-1-carboxylic acid (151907-79-8,108999-93-5)

Guidance literature:

With lipase B from Candida antarctica; In water; isopropyl alcohol; at 30 ℃; for 18h; stereospecific reaction; Enzymatic reaction;

DOI:10.1002/ejoc.200800723

Reference yield: 22.0%

→ (1S-cis)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-2-cyclopentene-1-carboxylic acid (151907-79-8,108999-93-5) + (1S,4R)-(-)-methyl-[[(1,1-dimethylethoxy)carbonyl]amino]cyclopent-2-ene-1-carboxylate (168683-02-1) + (1R,4R)-4-[(tert-butoxycarbonyl)amino]cyclopent-2-ene-1-carboxylic acid (298716-03-7,108999-93-5)

Guidance literature:

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

DOI:10.1016/j.tet.2003.10.116

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + (-)-(1S,4R)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride (130931-84-9) → (1S-cis)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-2-cyclopentene-1-carboxylic acid (151907-79-8,108999-93-5)

Guidance literature:

(-)-(1S,4R)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride; With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; water; at 0 ℃; for 0.0833333h;

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

upstream raw materials:

di-tert-butyl dicarbonate

(-)-(1S, 4R)-4-amino-2-cyclopentene-1-carboxylic acid

(-)-2-azabicyclo[2.2.1]hept-5-en-3-one

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

Downstream raw materials:

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

(1R,4S)-N-(tert-Butyloxycarbonyl)-1-amino-4-(hydroxymethyl)-2-cyclopentene

(1R,3S)-3-((tert-butoxycarbonyl)amino)cyclopentane-1-carboxylic acid

(+)-(4S)-4-aminocyclopent-1-ene-1-carboxylic acid

Refernces

• 1、 Rodriguez-Vazquez, Nuria,Salzinger, Stephan,Silva, Luis F.,Amorin, Manuel,Granja, Juan R.. "Synthesis of cyclic γ-amino acids for foldamers and peptide nanotubes". . p. 3477 - 3493. Retrieved 2013/07/11.
• 2、 -. "Novel Tricyclic Compounds". Page/Page column 68. . Retrieved 2009/12/27.