23460-73-3

Basic information

• Product Name: Alanine, N-(ethoxyoxoacetyl)-, ethyl ester
• Synonyms: N-Aethoxyoxalyl-DL-alanin-aethylester;ethyl-N-ethoxalyl-alaninate;N-Ethoxalyl-alaninethylester;Aethoxalyl-alanin-aethylester;N-ethoxyoxalyl-alanine ethyl ester;(1-Carboxyethyl)-oxamicacid-diethylester
• CAS NO: 23460-73-3
• Molecular Formula: C9H15NO5
• Molecular Weight: 217.222
• Mol File: 23460-73-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Alanine, N-(ethoxyoxoacetyl)-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Alanine, N-(ethoxyoxoacetyl)-, ethyl ester(23460-73-3)
• EPA Substance Registry System: Alanine, N-(ethoxyoxoacetyl)-, ethyl ester(23460-73-3)

Safety Data

• Hazardous Substances Data: 23460-73-3(Hazardous Substances Data)

Upstream product

• 95-92-1 oxalic acid diethyl ester 
• 302-72-7 rac-Ala-OH 
• 4755-77-5 Ethyl oxalyl chloride 
• 64-17-5 ethanol 
• 617-27-6 DL-alanine ethyl ester hydrochloride 

Downstream Products

• 5006-20-2 5-ethoxy-4-methyl-oxazole 
• 23429-04-1 4-methyl-5-ethoxy-2-oxazole carboxylate ethyl ester 

Relevant articles and documents

Preparation method of N-alkoxy oxalyl alanine ester

The invention discloses a preparation method of N-alkoxy oxalyl alanine ester, which comprises the following steps: (1) under the action of triphosgene and an organic alkali, carrying out an esterification reaction on alanine and an alcohol to obtain alanine ester hydrochloride; and (2) under the action of the organic alkali, carrying out an amidation reaction on the alanine ester hydrochloride obtained in the step (1) and oxalic ester, and after the reaction is finished, carrying out post-treatment to obtain the N-alkoxy oxalyl alanine ester. According to the preparation method, the triphosgene and the organic alkali are used as reaction additives, so that the use of toxic solvent benzene is avoided, the reaction time is shortened, the product purity and the reaction yield are high, and the preparation method is suitable for industrial production.

Synthesis of 4-hydroxy-6,9-difluorobenz[g]isoquinoline-5,10-diones and conversions to 4-hydroxy-6,9-bis[(aminoalkyl)amino]-benz[g]isoquinoline-5,10-diones

Synthetic procedures have been developed which lead to 4-hydroxy-6,9-difluorobenz[g]isoquinoline-5,10-dione (4a) and its 3-methyl analogue 4b. Attempts to displace the fluorides from 4a with N,N-dimethylethylenediamine were unsuccessful. Analogue 4a on treatment with N-(t-butoxycarbonyl)ethylene diamine led to 15, formed from addition of the nucleophilic amine to C-3. On the other hand, analogue 4b, on treatment with N,N-dimethylethylenediamine led to the anticipated difluoride displacement product 3c. The protection of the hydroxy group of 4a by benzylation with phenyldiazomethane led to 4c which on treatment with N-(t-butoxycarbonyl)ethylene diamine or N,N-dimethylethylenediamine led to the corresponding 6,9-bis-substituted analogues 18a and 18b, respectively. Reductive debenzylations of 18a and 18b by hydrogenation over Pearlman's catalyst also effected partial reductions of the quinone. However, air oxidation of the over reduced products led to 3a and 3b, respectively. Treatment of 3a with hydrogen chloride gas led to the hydrochloride salt of 3d. Addition of O-p-Methoxybenzyl-N,N'-diisopropylurea to 4a led to the p-methoxybenzyl analogue 4d. Treatment of 4d with N,N-dimethylethylene diamine or N-(t-butoxycarbonyl)ethylene diamine led to displacements of the fluorides to yield 18c and 18d, respectively. Deprotection of 18c to 3b was accomplished using methanesulfonic acid. Treatment of 18d with trifluoroacetic acid followed by addition of maleic acid led to dimaleate salt of 3d.