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US 6,333,416 B2Granted
(Oxazolin-4-yl) oxirane derivative
AssigneesJapan Tobacco Inc., Agouron Pharmaceuticals, Inc.
InventorsTakashi Inaba, Yasuki Yamada
Life of this patent
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Abstract
An (oxazolin-4-yl)oxirane derivative of formula [IX] wherein R4 is an optionally substituted alkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl or an optionally substituted heteroarylalkyl, an enantiomer thereof or a salt thereof.
Claims3
An (oxazolin-4-yl)oxirane derivative of the formula [XI]
- wherein R4 is an optionally substituted alkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl or an optionally substituted heteroarylalkyl, an enantiomer thereof or a salt thereof.
A method for producing an (oxazolin-4-yl)oxirane derivative of the formula [XI]
- wherein R4 is an optionally substituted alkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl or an optionally substituted heteroarylalkyl, or an enantiomer thereof, comprising treating an oxazoline derivative of the formula [X]
- wherein R4 is as defined above, R5 is a hydrogen atom or an acyl, and Z is a substituent which functions as a leaving group together with an oxygen atom, or an enantiomer thereof, with a base.
A method for producing an (oxazolin-4-yl)oxirane derivative of the formula [XI]
- wherein R4 is an optionally substituted alkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl or an optionally substituted heteroarylalkyl, or an enantiomer thereof, comprising reacting a (5R,6S)-6-amino-1,3-dioxepan-5-ol derivative of the formula [VI]
- wherein R1 and R2 are the same or different and each is a hydrogen atom, an alkyl or an aryl, or R1 and R2 combinedly form a cycloalkyl ring together with the adjacent carbon atom, an enantiomer thereof or a salt thereof, with a reactive carboxylic acid derivative having R4 wherein R4 is as defined above, in the presence of a base, to give a (5R,6S)-6-acylamino-1,3-dioxepan-5-ol derivative of the formula [VIII]
- wherein R1, R2 and R4 are as defined above, or an enantiomer thereof, reacting the resulting compound with a sulfonylating agent, treating with a Lewis acid, acylating, where necessary, to give an oxazoline derivative of the formula [X]
- wherein R4 is as defined above, R5 is a hydrogen atom or an acyl, and Z is a substituent which functions as a leaving group together with an oxygen atom, or an enantiomer thereof, and treating the obtained compound with a base.
1 more element
Dependencies are inferred from the claim text.