13756-47-3

Basic information

• Product Name: ETHOXYCARBONYLAMINO-ACETIC ACID METHYL ESTER
• Synonyms: ETHOXYCARBONYLAMINO-ACETIC ACID METHYL ESTER;Methyl 2-((ethoxycarbonyl)aMino)acetate;ETHYL (METHOXYCARBONYL)METHYLCARBAMATE
• CAS NO: 13756-47-3
• Molecular Formula: C₆H₁₁NO₄
• Molecular Weight: 161.15584
• Mol File: 13756-47-3.mol

Chemical Properties

• Boiling Point: 127-128 °C(Press: 14 Torr)
• Appearance: /
• Density: 1.124±0.06 g/cm3(Predicted)
• PKA: 11.04±0.46(Predicted)
• CAS DataBase Reference: ETHOXYCARBONYLAMINO-ACETIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: ETHOXYCARBONYLAMINO-ACETIC ACID METHYL ESTER(13756-47-3)
• EPA Substance Registry System: ETHOXYCARBONYLAMINO-ACETIC ACID METHYL ESTER(13756-47-3)

Safety Data

• Hazardous Substances Data: 13756-47-3(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 4596-51-4 N-(ethoxycarbonyl)glycine 
• 59943-88-3 5,5-dimethoxy-4,5-dihydro-[1,2,3]triazole-1-carboxylic acid ethyl ester 
• 124-38-9 carbon dioxide 
• 5680-79-5 glycine ethyl ester hydrochloride 
• 75-03-6 ethyl iodide 
• 541-41-3 chloroformic acid ethyl ester 
• 83643-84-9 methyl 4,4,4-trifluoroacetoacetate 
• 2955-74-0 ethyl N-{[(4-nitrobenzene)sulfonyl]oxy}carbamate 
• 67-56-1 methanol 
• 352294-50-9 [1-(ethoxycarbonylamino-methyl)-vinyl]-phosphonic acid diethyl ester 
• 56-40-6 glycine 

Downstream Products

• 3751-82-4 ethyl 1-ethoxycarbonyl-4-oxopyrrolidine-3-carboxylate 

Relevant articles and documents

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OXOBENZINDOLIZINOQUINOLINES AND USES THEREOF

The synthesis of aromathecins, substituted 12H-5,l la-diazadibenzo[b,h]fluoren- 11 -ones is described. Use of these cytotoxic compounds and pharmaceutical compositions containing them for the treatment of cancer is described. Two novel processes for the synthesis of this system and a series of 14-substituted aromathecins as novel cytotoxic, topoisomerase I poisons are described.

Design, synthesis, and biological evaluation of 14-substituted aromathecins as topoisomerase I inhibitors

The aromathecin or "rosettacin" class of topoisomerase I (top1) inhibitors is effectively a "composite" of the natural products camptothecin and luotonin A and the synthetic indenoisoquinolines. The aromathecins have aroused considerable interest following the isolation and total synthesis of 22-hydroxyacuminatine, a rare cytotoxic natural product containing the 12H-5,11a-diazadibenzo[b,h]fluoren-11-one system. We have developed two novel syntheses of this system and prepared a series of 14-substituted aromathecins as novel antiproliferative topoisomerase I poisons. These inhibitors are proposed to act via an intercalation and "poisoning" mechanism identical to camptothecin and the indenoisoquinolines. Many of these compounds possess greater antiproliferative activity and anti-top 1 activity than the parent unsubstituted compound (rosettacin) and previously synthesized aromathecins, as well as greater top1 inhibitory activity than 22-hydroxyacuminatine. In addition to potentially aiding solubility and localization to the DNA-enzyme complex, nitrogenous substituents located at the 14-position of the aromathecin system have been proposed to project into the major groove of the top1-DNA complex and hydrogen-bond to major-groove amino acids, thereby stabilizing the ternary complex.

A novel deacylation during the amination of trifluoromethyl β-dicarbonyl compounds

Starting from trifluoromethyl β-dicarbonyl compounds, a rare loss of CF3CO was observed in the amination reactions performed under heterogeneous conditions using NsONHCO2Et as the aminating agent and CaO or NaH as the base, while corresponding nonfluorinated β-dicarbonyl compounds under analogous conditions give non deacylated aminated compounds. This reaction can facilitate a direct synthesis of N-substituted α-amino esters or α-amino ketones.

Ozonization and reduction of α-methylene N-(ethoxycarbonyl)-β-amino phosphonic esters

N-(Ethoxycarbonyl)-β-amino-α-methylene phosphonic esters give N-(ethoxycarbonyl)-β-amino-α-hydroxy phosphonic esters by ozonization and subsequent reduction with a large excess of NaBH4. If there is a small excess of NaBH4 or if the intermediate is treated with methanolic NaOH-CH2Cl2 an anomalous ozonolysis occurs, affording N-(ethoxycarbonyl)-α-amino methyl carboxylic esters due to the cleavage of both the C=C double bond and the adjacent C-P single bond.

Convenient method for the synthesis of N-(ethyloxycarbonyl) ester derivatives from amino acids

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