2-diazo-3-[1-(methylphenylcarbamoyl)cyclopropyl]-3-oxopropionic acid ethyl ester

Base Information

Chemical Name:2-diazo-3-[1-(methylphenylcarbamoyl)cyclopropyl]-3-oxopropionic acid ethyl ester
CAS No.:299204-22-1
Molecular Formula:C₁₆H₁₇N₃O₄
Molecular Weight:315.329
Hs Code.:

Synonyms:2-diazo-3-[1-(methylphenylcarbamoyl)cyclopropyl]-3-oxopropionic acid ethyl ester

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Chemical Property of 2-diazo-3-[1-(methylphenylcarbamoyl)cyclopropyl]-3-oxopropionic acid ethyl ester

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Technology Process of 2-diazo-3-[1-(methylphenylcarbamoyl)cyclopropyl]-3-oxopropionic acid ethyl ester

There total 6 articles about 2-diazo-3-[1-(methylphenylcarbamoyl)cyclopropyl]-3-oxopropionic acid ethyl 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: 73.0%

: 299204-20-9
3-[1-(methylphenylcarbamoyl)cyclopropyl]-3-oxopropionic acid ethyl ester

: 299204-22-1
2-diazo-3-[1-(methylphenylcarbamoyl)cyclopropyl]-3-oxopropionic acid ethyl ester

Guidance literature:: With 4-toluenesulfonyl azide; triethylamine; In acetonitrile; for 12h;
DOI:10.1021/ja001088j

Reference yield:

: 3697-66-3
1,1-cyclopropanedicarboxylic acid monoethyl ester

: 299204-22-1
2-diazo-3-[1-(methylphenylcarbamoyl)cyclopropyl]-3-oxopropionic acid ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: oxalyl chloride; DMF / CH₂Cl₂ / 3 h / 20 °C

2.1: CH₂Cl₂ / 4 h / 20 °C

3.1: 85 percent / aq. KOH / ethanol / 4 h / 20 °C

4.1: oxalyl chloride; DMF / CH₂Cl₂ / 2 h / 20 °C

5.1: i-PrMgCl / CH₂Cl₂ / 1 h / 0 - 40 °C

5.2: 47 percent / CH₂Cl₂ / 2 h / 20 °C

6.1: 73 percent / tosyl azide; Et₃N / acetonitrile / 12 h

With potassium hydroxide; 4-toluenesulfonyl azide; oxalyl dichloride; isopropylmagnesium chloride; triethylamine; N,N-dimethyl-formamide; In ethanol; dichloromethane; acetonitrile; 1.1: Chlorination / 2.1: Acylation / 3.1: Hydrolysis / 4.1: Chlorination / 5.1: Metallation / 5.2: Acylation / 6.1: Diazotization;
DOI:10.1021/ja001088j

Reference yield:

: 3697-67-4
ethyl 1-chlorocarbonylcyclopropanecarboxylate

: 299204-22-1
2-diazo-3-[1-(methylphenylcarbamoyl)cyclopropyl]-3-oxopropionic acid ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: CH₂Cl₂ / 4 h / 20 °C

2.1: 85 percent / aq. KOH / ethanol / 4 h / 20 °C

3.1: oxalyl chloride; DMF / CH₂Cl₂ / 2 h / 20 °C

4.1: i-PrMgCl / CH₂Cl₂ / 1 h / 0 - 40 °C

4.2: 47 percent / CH₂Cl₂ / 2 h / 20 °C

5.1: 73 percent / tosyl azide; Et₃N / acetonitrile / 12 h

With potassium hydroxide; 4-toluenesulfonyl azide; oxalyl dichloride; isopropylmagnesium chloride; triethylamine; N,N-dimethyl-formamide; In ethanol; dichloromethane; acetonitrile; 1.1: Acylation / 2.1: Hydrolysis / 3.1: Chlorination / 4.1: Metallation / 4.2: Acylation / 5.1: Diazotization;
DOI:10.1021/ja001088j