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.
PROCESS FOR THE PREPARATION OF AMINO ACID DERIVATIVES
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Paragraph 0128; 0129; 0130; 0131, (2013/07/31)
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.
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.
Route development and multikilogram GMP delivery of a somatostatin receptor antagonist
Ruck, Rebecca T.,Huffman, Mark A.,Stewart, Gavin W.,Cleator, Ed,Kandur, Wynne V.,Kim, Mary M.,Zhao, Dalian
, p. 1329 - 1337 (2012/10/29)
Route development and demonstration on multikilogram scale for the first GMP delivery of MK-4256 are described. Key aspects of the convergent route include a regioselective green iodination, one-pot oxadiazole synthesis, and an efficient ketone Pictet-Spengler reaction with diastereomeric upgrade via crystallization to afford 6 kg of API. A recycle procedure augmented the yield of desired diastereomer in the Pictet-Spengler reaction from a mixture of diastereomers heavily enriched in the undesired diastereomer.
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.
PROCESSES FOR PRODUCTION OF PYRIMIDINE DERIVATIVES AND INTERMEDIATES
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Page/Page column 31-32, (2010/11/23)
Compound (I) is reacted with compound (II) to give compound (III), which is then reacted with compound (IX) to give compound (VIII), which is then preferably deprotected by an enzyme reaction to give compound (XII). The present invention provides an advan
Production method of aminopyrimidine compound
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Page/Page column 10, (2008/06/13)
Aminopyrimidine compounds represented by formula (3) may be efficiently prepared by reacting an azlactone compound represented by formula (1) with an amidine compound represented by formula (2) or a salt thereof: wherein R1, R2 and M are as defined in the specification.
Azlactone compound and method for preparation thereof
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Page/Page column 8, (2008/06/13)
The present invention provides a preparation method of a compound represented by the formula (II): wherein M is a hydrogen atom, sodium, potassium or lithium, P is a hydrogen atom, an alkyl group and the like and a wavy line shows a cis form, a trans form
Production method of pyrimidine derivative, intermediate therefor
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Page/Page column 38, (2010/02/11)
The present invention relates to a production method of compound (XV), which includes hydrolysis of compound (I) to give compound (II), then reaction with reagent (III) to give compound (IV), then reaction with compound (V) to give compound (VI), then con
