公开(公告)号：JP2002326982A

公开(公告)日：2002-11-15

申请号：JP2001099929

申请日：2001-03-30

Applicant: AJINOMOTO KK

Inventor： ONISHI TOMOYUKI ,  OTAKE YASUYUKI ,  KURODA SHINJI ,  HIROSE NAOKO ,  OKA SACHIKO ,  IZAWA KUNISUKE

IPC: C07C303/40 ,  C07B53/00 ,  C07B57/00 ,  C07C303/44 ,  C07C311/18

Abstract: PROBLEM TO BE SOLVED: To provide an economical and efficient method for producing a specific N-carbamate type protected benzenesulfonamide derivative which is suitable for industrial production, the specific benzenesulfonamide derivative and its salt derived from the aforesaid derivative and a method for producing a crystal of the benzenesulfonamide derivative salt. SOLUTION: An N-carbamate type protected β-aminoalcohol or an N- carbamate type protected β-aminoepoxide is reacted with N-isobutyl-3- nitrobenzenesulfonamide in the presence of a base to obtain the N-carbamate type protected benzenesulfonamide derivative. In the benzenesulfonamide derivative in which a protecting group of the amino group is benzyloxycarbonyl group, the protecting group is removed by reacting methanesulfonic acid. An impurity is efficiently separated and removed into the mother liquor by crystallizing a methanesulfonate of the benzenesulfonamide derivative containing at least a diastereomer thereof as the impurity from an alcohol or an alcoholic mixed solvent.

公开(公告)号：JP2002332270A

公开(公告)日：2002-11-22

申请号：JP2001132844

申请日：2001-04-27

Applicant: AJINOMOTO KK

Inventor： ONISHI TOMOYUKI ,  KURODA SHINJI ,  OTAKE YASUYUKI ,  OKA SACHIKO

IPC: C07C269/08 ,  C07B53/00 ,  C07C271/20 ,  C07C303/38 ,  C07C303/40 ,  C07C311/18

Abstract: PROBLEM TO BE SOLVED: To provide a method of producing a compound of formula 1 or formula 2 that is suitable for industrial production and provide a method of producing a specific benzenesulfonamide derivative or salt thereof. SOLUTION: Water is added to a polar solvent including a compound of formula 1 or formula 2 dissolved in to crystallize out (2R,3S)-3- benzyloxycarbonylamino-2-hydroxy-1-(N-isobutyl)-amino-4-phenylbutane or (2S,3 R)-3-benzyloxycarbonylamino-2-hydroxy-1-(N-isobutyl)amino-4-phenylbutane. Further, methanesulfonic acid is allowed to act on N-benzyloxycarbonyl- protected benzenesulfonamide derivative to deprotect the benzyloxycarbonyl group.