188663-05-0Relevant articles and documents
Aminoacids in the Synthesis of Heterocyclic Systems. the Synthesis of Methyl 2-Acetylamino-3-dimethylaminopropenoate and 2-(N-Methyl-N-trifluoroacetyl)amino-3-dimethylaminopropenoate and their Application in the Synthesis of Heterocyclic Compounds
Kralj, Lucija,Hvala, Ales,Svete, Jurij,Golic, Ljubo,Stanovnik, Branko
, p. 247 - 255 (1997)
Methyl (Z)-2-acctylamino-3-dimethylaminopropenoate (3) was prepared from N-acetylglycine (1), which was converted with N,N-dimethylfonnamide and phosphorus oxychloride into 4-dimethylaminomethylene-2-methyl-5(4H)-oxazolone (2), followed by treatment with methanol in the presence of potassium carbonate, into 3 The compound 3 was shown to be a versatile reagent in the synthesis of various heterocyclic systems. With N-nucleophiles, such as heterocyclic amines 4, either methyl 2-acetylamino-3-heteroarylaminopropenoates 5 or fused pyrimidinones 6 were formed, dependent on the reaction conditions and/or heterocyclic substituent: C-nucleophiles with an active or potentially active methylene group, such as 1,3-dicarbonyl compounds 7, 8 and 9, substituted phenols 10a,b, naphthols 11,12a-c, and substituted coumarin 13a, afforded substituted pyranones 20 and 22, and fused pyranones 21, 23-26. The nitrogen containing heterocycles 14-19 produced pyranoazines 27-31 and pyranoazole 32. In all of these systems the acetylamino group is attached at position 3 of the newly formed pyranone ring. The orientation around the double bond for methyl (Z)-2-(N-methyl-N-trifluoroacetyl)-3-dimethylaminopropenoate (36) was established by X-ray analysis.
An improved synthesis of 5-acylamino-6-oxo-2-phenyl-1(6h)-pyrimidineacetic acid from glycine with readily removable protecting groups
Takahashi, Daisuke,Izawa, Kunisuke,Kashiwagi, Tatsumi,Onoye, Hiromi,Williams, Robert M.
, p. 2213 - 2229,17 (2020/08/31)
Concise synthesis of N-acyl-5-amino-6-oxo-2-phenyl-1(6H)- yrimidineacetic acid was achieved by cyclization reaction of 2-alkyl-4- lkoxymethylene-5(4H)- oxazolone with N-(carboxymethyl)benzamidine, while a similar reaction with sodium salt of 2-alkyl-4-hydroxymethylene-5(4H)- xazolones gave a mixture of regioisomers of the pyrimidinone. N-Acyl groups (acetyl or phenylacetyl) of the pyrimidinone derivatives were readily cleaved under very mild conditions with weak base or enzyme. Thus, the process enabled us to synthesize the drug candidate without exchanging N-protecting group. Since the starting oxazolones were easily prepared from N-acylglycine, the synthetic route can be used for the large scale synthesis of the key intermediate for several enzyme inhibitors.
PROCESS FOR THE PREPARATION OF AMINO ACID DERIVATIVES
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Page/Page column 23, (2012/04/17)
The present invention relates to a process of manufacture of compounds of formula (B) wherein R1, R2 and R3 are as defined for compounds of formula (A), which process comprises hydrogenation of compounds of general formula (A). In particular, the present invention relates to an improved process for the manufacture of Lacosamide (LCM), (R)-2-acetamido-N-benzyl-3-methoxypropion-amide (B1), which is useful as an anticonvulsive drug.
