(1R,4S)-rel-4-(AcetylaMino)-2-cyclopentene-1-carboxylic Acid Methyl Ester

Base Information

• Chemical Name: (1R,4S)-rel-4-(AcetylaMino)-2-cyclopentene-1-carboxylic Acid Methyl Ester
• CAS No.: 61865-49-4
• Molecular Formula: C₉H₁₃NO₃
• Molecular Weight: 183.207
• Mol file: 61865-49-4.mol

Synonyms:methyl (1S,4R)-4-acetamidocyclopent-2-ene-1-carboxylate;

Chemical Property of (1R,4S)-rel-4-(AcetylaMino)-2-cyclopentene-1-carboxylic Acid Methyl Ester

Chemical Property:

• PSA: 58.89000
• LogP: 1.08050
• Solubility.: Chloroform, Dichloromethane, DMSO, Methanol

Purity/Quality:

97% ^*data from raw suppliers

(1R,4S)-rel-4-(Acetylamino)-2-cyclopentene-1-carboxylicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Carbovir intermediate.

Technology Process of (1R,4S)-rel-4-(AcetylaMino)-2-cyclopentene-1-carboxylic Acid Methyl Ester

There total 11 articles about (1R,4S)-rel-4-(AcetylaMino)-2-cyclopentene-1-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: 84.0%

lead(IV) tetraacetate (546-67-8) + (1R,4S)-4-Carbamoyl-cyclopent-2-enecarboxylic acid methyl ester → ester methylique de l'acide (acetamido-cis-4)-cyclopentene-2-carboxylique (61865-49-4,69919-17-1,86252-76-8,127061-46-5)

Guidance literature:

With acetic acid; for 1h; Heating;

Reference yield:

acetic anhydride (108-24-7) + (cis)-methyl 4-aminocyclopent-2-enecarboxylate (152279-17-9,352226-74-5,773006-65-8) → ester methylique de l'acide (acetamido-cis-4)-cyclopentene-2-carboxylique (61865-49-4,69919-17-1,86252-76-8,127061-46-5)

Guidance literature:

With pyridine; for 1h; Yield given; Ambient temperature;

DOI:10.1016/S0957-4166(00)86183-2

Reference yield:

meso-cyclopent-4-ene-1,3-dicarboxylic acid (30213-23-1) → ester methylique de l'acide (acetamido-cis-4)-cyclopentene-2-carboxylique (61865-49-4,69919-17-1,86252-76-8,127061-46-5)

Guidance literature:

Multi-step reaction with 3 steps

1: DCC / CH₂Cl₂

2: 1.) NH₃, 2.) SOCl₂, Na₂CO₃

3: 84 percent / AcOH / 1 h / Heating

With thionyl chloride; ammonia; sodium carbonate; acetic acid; dicyclohexyl-carbodiimide; In dichloromethane;

upstream raw materials:

lead(IV) tetraacetate

acetic anhydride

(cis)-methyl 4-aminocyclopent-2-enecarboxylate

cis-4-amino-2-cyclopentenecarboxylic acid methyl ester hydrochloride

Downstream raw materials:

N-((1R,4S)-4-Hydroxymethyl-cyclopent-2-enyl)-acetamide

(+/-)-trans-4-(2-amino-6-chloro-9-H-purin-9-yl)-2-cyclopentene-1-methanol

(-)-(1R,2R,3S,4R)-4-amino-2,3-dihydroxy-1-(hydroxymethyl)cyclopentane

(1β,2β,3α,5α)-5-Amino-3-hydroxymethyl-1,2-cyclopentanediol