Process for producing optically active α-fluorocarboxylate
AssigneeCentral Glass Company, Limited
InventorsAkihiro Ishii, Hideyuki Tsuruta, Yuzuru Morino, Mikihiro Takahashi
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Abstract
An optically active α-fluorocarboxylate is produced by reacting an optically active α-hydroxycarboxylate with sulfuryl fluoride (SO2F2), trifluoromethanesulfonyl fluoride (CF3SO2F) or nonafluorobutanesulfonyl fluoride (C4F9SO2F) in the presence of organic base and in the absence of reaction solvent. More preferably, a distillation purification is conducted after adding acid to the reaction-terminated liquid. With this, it is possible to produce an optically active α-fluorocarboxylate of a still higher purity. It is possible by this process to advantageously produce an optically active α-fluorocarboxylate on a large-amount scale.
Claims9
A process for producing an optically active α-fluorocarboxylate represented by formula [2]
- wherein R1 represents a C1-6 alkyl group, R2 represents a C1-4 alkyl group, and * represents an asymmetric carbon, the process comprising reacting an optically active α-hydroxycarboxylate represented by formula [1]
- wherein R1, R2 and * are defined as above, with sulfuryl fluoride (SO2F2), trifluoromethanesulfonyl fluoride (CF3SO2F) or nonafluorobutanesulfonyl fluoride (C4F9SO2F), in the presence of organic base and in the absence of reaction solvent,
- wherein stereochemistry of the asymmetric carbon in formula [1] is inverted by the reaction.
A process for producing an optically active 2-fluoropropionate represented by formula [4]
- wherein R represents a methyl group or ethyl group, and * represents an asymmetric carbon, the process comprising reacting an optically active lactate represented by formula [3]
- wherein R and * are defined as above, with sulfuryl fluoride (SO2F2) or trifluoromethanesulfonyl fluoride (CF3SO2F), in the presence of an organic base selected from the group consisting of triethylamine, diisopropylethylamine, tri-n-propylamine, tri-n-butylamine, tri-n-pentylamine, tri-n-hexylamine, pyridine, 2,3-lutidine, 2,4-lutidine, 2,6-lutidine, 3,4-lutidine, 3,5-lutidine, 2,4,6-collidine, and 3,5,6-collidine, and in the absence of reaction solvent
- wherein stereochemistry of the asymmetric carbon in formula [3] is inverted by the reaction.
A process for producing methyl (R)-2-fluoropropionate represented by formula [6]
- the process comprising reacting methyl (S)-lactate represented by formula [5]
- with sulfuryl fluoride (SO2F2), in the presence of triethylamine or tri-n-butylamine and in the absence of reaction solvent.
Dependencies are inferred from the claim text.