Organic compounds -- part of the class 532-570 series – Organic compounds – Sulfur containing
Patent
1997-06-30
2000-04-11
Geist, Gary
Organic compounds -- part of the class 532-570 series
Organic compounds
Sulfur containing
C07C31914
Patent
active
060490098
DESCRIPTION:
BRIEF SUMMARY
This is the national phase of PCI/JP96/03185, filed Oct. 30, 1996.
TECHNICAL FIELD
The present invention relates to a method for producing an optically active trans-vinylsulfide alcohol useful as a synthetic material of penem or carbapenem compounds.
BACKGROUND ART
Various researches have heretofore made for penem or carbapenem compounds, since they have wide and strong antimicrobial activities. In the production thereof, (1'R, 3R, 4R)-3-(1'-protected hydroxyethyl)-4-acyloxy-2-azetidinone derivatives (i.e., "acyloxyazetidinone derivatives" hereinbelow) are used as an excellent synthetic intermediate and various synthetic methods are reported (see N. Ueyama et al., JP-A-62-84057).
At present, as a production method of acyloxyazetidinone derivatives, the following method is known (see JP-A-3-127773). ##STR2## wherein OR represents a protected hydroxy group, X represents an alkyl or aryl group, and Y represents an acyl group.
Thus, this method is a method capable of safe and efficiently producing the desired acyloxyazetidinone derivatives (V) by reacting (1'R, 3S, 4R)-3-(1'-protected hydroxyethyl)-4-substituted thio-2-azetidinone derivatives (IV) (i.e., "substituted thioazetidinone derivatives" hereinbelow) with a carboxylic acid in the presence of a copper compound.
As explained above, although acyloxyazetidinone derivatives useful as a synthetic intermediate of penem or carbapenem compounds can be produced in an industrial scale from the substituted thioazetidinone derivatives as a starting material, there are various problems in the known methods for producing the starting substituted thioazetidinone derivatives. ##STR3## wherein Hal represents a halogen atom, R.sup.1 represents an alkyl or aryl group, and OR and Y are the same as defined above.
According to the above-mentioned method (see JP-A-61-207373), an optically active 1,3-butanediol (VI) is used as a starting material and the substituted thioazetidinone derivatives (XI) can be obtained at a high yield from the cyclization reaction, with chlorosulfonyl isocyanate (CSI), of the intermediate trans-vinylsulfide (IX) obtained from the starting material through the steps of the substitution at the 1-position, the protection of the hydroxy group at the 3-position, the halogenation and the dehydrohalogenation. This is an excellent method. However, according to the above method, there are still problems that the starting optically active 1,3-butanediol is expensive and also, since the multi-step synthesis is necessary for producing the trans-vinylsulfide (IX), there are problems in the yield thereof. Furthermore, the cis-isomer (X), which is produced as a by-product during the synthesis of the trans-vinylsulfide (IX) and which is extremely difficult to separate from the trans-isomer, affects the selectivity and yield of the subsequent cyclization reaction.
Furthermore, a method for obtaining an optically active 1-substituted-3-hydroxybutane or optically active 1-substituted-3-hydroxybutene from the optical resolution of the ester derivative of racemic 1-substituted-3-hydroxybutane or racemic 1-substituted-3-hydroxybutene, respectively, with lipase (see JP-A-4-228092 and JP-A-4-228093). This method is an effective method in view of the excellent selectivity, but the maximum yield of the optically active substance is as high as 50%.
As mentioned above, there are various problems to be solved in the conventional production method for obtaining the substituted thioazetidinone derivatives and there are strong need to solve these problems.
SUMMARY OF THE INVENTION
The objects of the present invention are to solve the above-mentioned problems in the prior art and to provide a method for industrially producing an optically active trans-vinylsulfide alcohol, which is useful as a synthetic material of penem or carbapenem compounds, effectively at a low cost under mild conditions.
In accordance with the present invention, there is provided a method for producing an optically active trans-vinylsulfide alcohol having the formula (III): ##STR4## wherein R.sup.1
REFERENCES:
patent: 5039802 (1991-08-01), Blacklock et al.
patent: 5264585 (1993-11-01), Blacklock
J of Org Chem , 58(4), pp. 799-801, "Origins of the Enantioselectivity Observed in Oxazaborolidine-Catalyzed Reducions of Ketones", Feb. 1993.
CA:91:39069 abstract of Chem Lett (4) pp. 365-368 of "Reduction of beta alkylthio alpha beta unsaturated ketones with lithium tetrahydroaluminate or sodium tertahydroborate", 1979.
CA:108:75026 abstract of J Am Chem soc 109(25) pp. 7925-7926 of "A stable and easily prepared catalyst for the enantioselective reduction of ketones", 1987.
E.J. Corey et al., "A New System for Catalytic Enantioselective Reduction of A Chiral Ketones to Chiral Alcohols. Synthesis of Chiral .alpha.-Hydroxy Acids", Tetrahedron Letters, vol. 31., No. 5, pp. 611-614, (1990).
Imoto Masahiro
Inoue Hidekazu
Ishiguro Masaji
Nakatsuka Takashi
Sekiuchi Kazuto
Geist Gary
Suntory Limited
Vollano Jean F
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