PROCESSES FOR PRODUCING BETA-HALOGENO-ALPHA-AMINO-CARBOXYLIC ACIDS AND PHENYLCYSTEINE DERIVATIVES AND INTERMEDIATES THEREOF
申请人:KANEKA CORPORATION
公开号:EP1046634A1
公开(公告)日:2000-10-25
An industrially advantageous method of producing β-halogeno-α-aminocarboxylic acids is provided. Methods are also provided of producing optically active N-protected-S-phenylcysteines having high optical purity and of intermediates thereof, respectively, in which the above production method is utilized.
A method of producing β-halogeno-α-aminocarboxylic acids or salts thereof is disclosed which comprises halogenating the hydroxyl group of a β-hydroxy-α-aminocarboxylic acid (in which the basicity of the amino group in α-position is not masked by the presence of a substituent on said amino group) or a salt thereof with an acid with a halogenating agent. A method of producing optically active N-protected-S-phenylcysteines represented by the general formula (3) or salts thereof is further disclosed which comprises applying the above production method to optically active serine or a salt thereof and then carrying out treatment with an amino-protecting agent and reaction with thiophenol under a basic condition.
本发明提供了一种具有工业优势的生产 β-卤代-α-氨基羧酸的方法。此外,还提供了利用上述生产方法分别生产具有高光学纯度的光学活性 N-保护-S-苯基半胱氨酸及其中间体的方法。
本发明公开了一种生产 β-卤代-α-氨基羧酸或其盐的方法,该方法包括将 β-羟基-α-氨基羧酸(其中 α 位氨基的碱性不因所述氨基上取代基的存在而被掩盖)的羟基或其盐与含有卤化剂的酸进行卤化。进一步公开了一种生产通式(3)代表的光学活性 N-保护-S-苯基半胱氨酸或其盐的方法,该方法包括将上述生产方法应用于光学活性丝氨酸或其盐,然后用氨基保护剂进行处理,并在碱性条件下与噻吩酚反应。