Abstract:
The application is concerned with a process for producing a 3-hydroxytetrahydrofuran of the formula (3): by cyclizing a 4-halo-1,3-butanediol of the general formula (2): wherein X represents a halogen atom in an aqueous solution, which comprises carrying out the cyclization reaction under weakly acidic to neutral conditions. Furthermore several methods are disclosed for the isolution of highly pure 3-hydroxytetrahydrofuran.
Abstract:
An optically active amino acid derivative is produced by N-protecting an optically active 3-haloalanine derivative followed by cyclization, or cyclizing this derivative followed by N-protection to thereby give an optically active N-protected-aziridine-2-carboxylic acid derivative which is protected by a benzenesulfonyl group substituted by nitro at the 2- and/or 4-positions and then treating this product with an organic metal reagent, or by N-protecting an optically active 3-haloalanine derivative to thereby give N-protected-aziridine-2-carboxylic acid which is protected by a benzenesulfonyl group substituted by nitro at the 2- and/or 4-positions and then treating this product with an organic metal reagent. According to this process, natural and unnatural optically active amino acids can be produced from inexpensive materials by using simple procedures.
Abstract:
An optically active amino acid derivative is prepared either by subjecting a n optically active 3-haloalanine derivative (1) to N-protection followed by cyclization or cyclization followed by N-protection to prepare an optically active aziridinecarboxylic acid derivative (3) whose imino group is protecte d with 2- and/or 4-nitrated benzenesulfonyl and treating this derivative (3) with an organometallic reagent or by subjecting an optically active 3- haloalanine derivative to N-protection to obtain an optically active 3- haloalanine derivative (4) whose amino group is protected with 2- and/or 4- nitrated benzenesulfonyl and treating this derivative (4) with an organometallic reagent. According to such processes, natural and nonnatural optically active amino acids can be prepared from inexpensive raw materials through simple and easy operation. In said derivatives, X is halogen; R1 and R2 are each hydrogen or the like; * represents an asymmetric carbon atom; an d P1 is 2- and/ or 4- nitrated benzenesulfonyl.
Abstract:
The application is concerned with a process for producing a 3-hydroxytetrahydrofuran of the formula (3): by cyclizing a 4-halo-1,3-butanediol of the general formula (2): wherein X represents a halogen atom in an aqueous solution, which comprises carrying out the cyclization reaction under weakly acidic to neutral conditions. Furthermore several methods are disclosed for the isolution of highly pure 3-hydroxytetrahydrofuran.
Abstract:
An optically active amino acid derivative is prepared either by subjecting an optically active 3-haloalanine derivative (1) to N-protection followed by cyclization or cyclization followed by N-protection to prepare an optically active aziridinecarboxylic acid derivative (3) whose imino group is protected with 2- and/or 4-nitrated benzenesulfonyl and treating this derivative (3) with an organometallic reagent or by subjecting an optically active 3-haloalanine derivative to N-protection to obtain an optically active 3-haloalanine derivative (4) whose amino group is protected with 2- and/or 4-nitrated benzenesulfonyl and treating this derivative (4) with an organometallic reagent. According to such processes, natural and nonnatural optically active amino acids can be prepared from inexpensive raw materials through simple and easy operation. In said derivatives, X is halogen; R?1 and R2¿ are each hydrogen or the like; * represents an asymmetric carbon atom; and P1 is 2- and/ or 4- nitrated benzenesulfonyl.
Abstract:
A process for preparing optically active azetidine -2-carboxylic acid efficiently, easily, simply, and industrially advantageously by cyclizing an optically active 4-amino- 2-halogenobutyric acid in an optical yield of as high as 90 % or above. Specifically, a process for preparing optically active azetidine-2-carboxylic acid of formula (2) (wherein * represents an asymmetric carbon atom) by cyclizing an optically active 4-amino-2-halogenobutyric acid of the general formula (1) (wherein X is halogeno and * represents an asymmetric carbon atom) in the presence of an alkaline earth metal oxide, an alkaline earth metal hydroxide except barium hydroxide, or an organic amine.
Abstract:
PROBLEM TO BE SOLVED: To provide high-purity 3-hydroxytetrahydrofuran in a high yield easily and simply by an industrially advantageous process. SOLUTION: The process includes: reducing a 4-halo-3-hydroxybutyric acid ester with a boron hydride compound and/or an aluminum hydride compound in an organic solvent immiscible with water; treating the reaction mixture with an acid and water to convert it into the corresponding 4-halo-1, 3-butanediol and at the same time obtaining an aqueous solution containing the compound; carrying out the cyclization reaction in the aqueous solution; extracting the resulting 3-hydroxytetrahydrofuran from the aqueous solution using an organic solvent immiscible with water; and isolating the 3-hydroxytetrahydrofuran by concentration and/or distillation of the solution obtained. COPYRIGHT: (C)2010,JPO&INPIT