Malonic acid, monoethyl ester, potassium

Isobutyryl chloride (8) Propanoyl chloride, 2-methyl (9) (79-30-1) Potassium monoethylmalonate Malonic acid, monoethyl ester, potassium salt (8) Propanedioic acid, monoethyl ester, potassium salt (9) (6148-64-7)... 

The synthesis of the moxifloxacin core (de Souza, 2006 Martel et al., 1997 Seidel et al., 2000) proceeds from a Grohe-Heitzer sequence as described earlier in the chapter. Unlike the traditional Grohe-Heitzer sequence, however, the opening step involved the reaction between acid chloride 101 with the mono potassium salt of malonic acid monoethyl ester (102) in the presence of triethylamine to deliver ketoester 103 (Scheme 4.18). Treatment of 103 with ethyl orthoformate furnished acrylate 104, which reacted with cyclopropyl amine to afford 105. Cyclization of 105 in the presence of sodium fluoride in DMF gave the moxifloxicin core 106. 

Adipic acid has been prepared by the following methods the action of silver1 or copper 2 on /3-iodopropionic acid the reduction of mucic add with phosphorus and iodine 3 the electrolysis of the potassium or sodium salts of monoethyl succinate 4 the condensation of ethylene chloride or bromide with malonic ester or cyanoacetic ester and subsequent hydrolysis 5 the oxidation of certain fractions of Baku petroleum 6 the oxidation of cyclohexanol or cyclohexanone with nitric acid 7 or potassium permanganate.8... 

Malonic acid, ethyl malonate, and their monoalkyl derivatives can be readily halogenated in ether solution subsequent decarboxylation leads to the corresponding a-halogenated acetic acid in 55-80% yield. The reaction of the potassium salts of monoethyl alkylmalonates with bromine provides the a-bromo esters directly, although the yields ate relatively low. ... 

The (ethyloxycarbonyl)methanide ion is produced in the reaction mixture from the potassium salt of the monoethyl ester of the malonic acid. Ring opening by cleavage of the N-S bond is followed by cyclization and / -elimination. This results in a ring transformation to give substituted thiophenes. 

Stepwise Degradation to Amino Adds. There are several approaches to the transformation of a di- or poly-carboxylic acid to an amino acid. The most satisfactory procedure makes use of the ester acids and their salts. They react with hydrazine to form hydrazide acids, which may be degraded through the azide acids to amino acids. From substituted malonic esters a-amino acids are obtained. (For the preparation of a-amino acids from substituted cyanoacetic esters, see p. 359.) Thus, the potassium salt of the monoethyl ester of methylmalonic acid, which is prqjared by half hydroly of the diethyl ester, pves alanine ethyl ester hydrochloride in 67% yield. Many other amino acids have... 

Similarly, reaction of 321 with cyanoacetic ester and potassium carlxtnate gave the benzopyrane 322. When ketone 321 was treated with monoethyl malonate, triethylamine and phenyl phosphorodichloridate, the required coumarin 323a was obtained and subsequent alkaline hydrolysis gave the acid 323b [179] (Scheme 103). 

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