Abstract:
PROBLEM TO BE SOLVED: To obtain a new 5,5-dialkoxy-2-oxazolidinone compound useful as an intermediate for producing α-amino acid esters which are the technical products or intermediates of medicines.agrochemicals and easily giving the α-amino acid esters in high yields. SOLUTION: A compound of formula I [R1 is H, a 1-10C alkyl or the like; R2 is H, phenyl or the like; R3 is a 1-10C alkyl, a 3-10C cycloalkyl or the like; R4 is H or a group of formula II (R6 is H, a 2-10C alkenyl or the like; R7 is a 1-10C alkyl, phenyl or the like); R5 is phenyl, a 2-10C alkenyl or the like], for example, 3-diphenylmethyl-4-(1-methoxy-1-phenylmethyl)-5,5-dimethoxy-2- oxazolidinone. The compound of formula I is obtained by reacting a 5-alkoxy-2(3 H)-oxazolone compound of formula III with an oxygen-containing organic compound of the formula: R4-OR5 (preferably benzaldehyde dimethylacetal, etc.), in the presence of a catalyst (preferably trifluoromethane sulfonic acid, etc.).
Abstract:
PROBLEM TO BE SOLVED: To obtain the subject new compound useful as a starting substance on the syntheses of quinolone carboxylic acid compounds useful as medicines, especially antibacterial agents and antiviral agents. SOLUTION: A compound of formula I (R is H, a 1-10C alkyl, a 3-10C cycloalkyl or the like), e.g. 2,3,4-trifluoro-5-trifluoromethylbenzoic acid ethyl ester. The compound of formula I is obtained by reacting a 2, 3, 4-trifluoro-5- iodobenzoic acid ester of formula II (R is a 1-10C alkyl, a 3-10C cycloalkyl or the like) (preferably 2,3,4-trifluoro-5-iodobenzoic acid 1-4C alkyl ester) with a fluorosulfonyldifluoroacetic ester of formula III (preferably a fluorosulfonyldifluoroacetic acid 1-4C alkyl ester) in the presence of a copper catalyst (preferably cuprous iodide) in an organic solvent (preferably dimethylformamide, dimethylacetamide).
Abstract:
PROBLEM TO BE SOLVED: To provide a method for producing the subject compound useful as a starting material for antibacterial and antiviral medicines by reacting a specific ester with a 2,4,5-trifluoro-3-iodobenzoate. SOLUTION: This method reacts a 2,4,5-trifluoro-3-iodobenzoate shown by formula I (R is an alkyl, cycloalkyl or the like) with a 2,2-difluoro(fluorosulfonyl) acetate shown by formula II in the presence of a copper catalyst, such as cuprous iodide, in an organic solvent, such as dimethylformamide, to produce a 2,4,5-trifluoro-3-trifluoromethylbenzoate shown by formula III as the objective compound. It can be produced at 0 to 200 deg.C and in a high yield without risk of explosion.
Abstract:
PROBLEM TO BE SOLVED: To industrially obtain in high yield the subject compound important as a raw material for producing medicines and agrochemicals (esp. medicines). SOLUTION: An arylacetic acid of the formula R CH2 COOH (I) [R is (alkyl- or halogen-substituted) phenyl or 2-thienyl] is reacted with a haloalkylmagnesium of the formula R MgX (II) (R is an alkyl; X is a halogen atom) in an organic solvent followed by reaction with a cyclopropanecarboxylic ester of the formula R COOR (III) [R is a (alkyl- or fluorine-substituted) cyclopropyl group; R is an alkyl] to obtain the objective aryl cyclopropyl ketone of the formula R CH2 COR (IV). In this case, 2.5-5mol equivalent of the Grignard reagent (II) based on the arylacetic acid (I) is used.
Abstract:
PURPOSE: To obtain α-aminoketone under mild condition in high yield and selectivity by an aminolysis reaction using an α,β-epoxysulfone and a secondary amine. CONSTITUTION: The objective α-aminoketone of formula III is produced by reacting (A) an α,β-epoxysulfone of formula I (R and R are each H or a hydrocarbon group such as a 1-10C alkyl, a 3-10C cycloalkyl, a 2-10C alkenyl or a 7-12C aralkyl; R is a hydrocarbon group same as R and R except for H; R is a hydrocarbon group such as a 1-10C alkyl or a 7-12C aralkyl) with (B) a secondary amine of formula II (R and R are each a hydrocarbon group selected from a 1-10C alkyl, a 2-10C alkenyl and a 7-12C aralkyl or R and R together form a heterocyclic group which may have substituent) or its salt in the presence of a base in an organic solvent. The α-aminoketone is useful as a synthetic intermediate for an antithrombotic agent having blood platelet coagulation inhibiting action.
Abstract:
The present invention provides: a method for producing a mixed sulfonic acid anhydride of the general formula (1) by reacting a sulfonic acid compound of the general formula (2) with a perfluoroalkyl sulfonic acid anhydride or a perfluoroalkyl sulfonic acid halide; and a method for producing a sulfonamide compound of the general formula (4) obtained by reacting an amine compound of the general formula (3) with a mixed sulfonic acid anhydride of the general formula (1).
Abstract:
3-Amino-3-arylpropionic acid n-alkyl esters represented by the general formula (I); a process for the production of the same; and optical isomers thereof: (I) [wherein Ar1 is optionally substituted aryl exclusive of phenyl and 4-methoxyphenyl; and R1 is n-propyl or n-butyl], and a process for the production of optically active (S or R)-3-amino-3-arylpropininc acids represented by the general formula (III-a): (III-a) [wherein Ar is optionally substituted aryl; and * is an asymmetric carbon] and optically active (R or S)-3-amino-3-arylpropionic acid n-alkyl esters represented by the general formula (IV-a): (IV-a) [wherein Ar, R1 and * are each as defined above, with the proviso that each ester has an absolute configuration opposite to that of the compound (III-a)].