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KR950014123A - Separation method of diastereomer of asymmetric 3-methoxymethyl cephalosporin derivative - Google Patents

Separation method of diastereomer of asymmetric 3-methoxymethyl cephalosporin derivative Download PDF

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Publication number
KR950014123A
KR950014123A KR1019930024602A KR930024602A KR950014123A KR 950014123 A KR950014123 A KR 950014123A KR 1019930024602 A KR1019930024602 A KR 1019930024602A KR 930024602 A KR930024602 A KR 930024602A KR 950014123 A KR950014123 A KR 950014123A
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South Korea
Prior art keywords
formula
compound
diastereomer
optically pure
form structure
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KR1019930024602A
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Korean (ko)
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KR970004048B1 (en
Inventor
김완주
정명희
조귀웅
Original Assignee
강박광
재단법인 한국화학연구소
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Priority to KR1019930024602A priority Critical patent/KR970004048B1/en
Publication of KR950014123A publication Critical patent/KR950014123A/en
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Publication of KR970004048B1 publication Critical patent/KR970004048B1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/02—Preparation
    • C07D501/12—Separation; Purification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/14—Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/18—7-Aminocephalosporanic or substituted 7-aminocephalosporanic acids

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Cephalosporin Compounds (AREA)

Abstract

본 발명은 다음 일반식(Ⅰ)의 세팔로스포린 유도체의 디아스테레오머를 분리 제조하는 방법에 관한 것으로, 더욱 상세하게는 경구용 항생제의 중간체로 유용한 다음 일반식(Ⅰ)의 1-2, 2-디메틸프로파노일옥시)에틸 7-아미노-3-메톡시메틸-3-세팸-4-카르복실산염 형태의 디아스테레오머 혼합물을 순수한 단일 디아스테로오머로 각각 분리하는 제조방법이다.The present invention relates to a method for separating and preparing a diastereomer of the cephalosporin derivative of the following general formula (I), and more particularly, 1-2, 2 of the following general formula (I) useful as an intermediate of an oral antibiotic -Dimethylpropanoyloxy) ethyl 7-amino-3-methoxymethyl-3-cepam-4-carboxylate form of diastereomer mixture, each separated into a pure single diastereomer.

윗식에서, X-는 C1-또는이다In the above formula, X- is C1- or to be

Description

비대칭형 3-메톡시메틸 세팔로스포린 유도체의 디아스테레오머의 분리방법Separation method of diastereomer of asymmetric 3-methoxymethyl cephalosporin derivative

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

Claims (2)

일반식(I)의 토실레이트 염화합물의 디아스테레오머 혼합물을 CHCl3로 재결정하여 광학적으로 순수한 (S)-form 구조의 일반식(Ia)의 화합물을 분리하여 제조하고, 이어서 상기의 재결정후에 남은 CHCl3용액을 농축 및 재결정하여 광학적으로 순수한 (R)-form 구조의 일반식(Ib)의 화합물을 분리하는 것을 특징으로 하는 제조방법.A diastereomer mixture of the tosylate salt compound of formula (I) is recrystallized from CHCl 3 to prepare a compound of formula (Ia) having an optically pure (S) -form structure, and then remaining after the recrystallization. Concentrating and recrystallizing the CHCl 3 solution to separate the compound of formula (Ib) of the optically pure (R) -form structure. 윗 식에서, X-는 Cl-또는이다.In the above formula, X - is Cl - or to be. 일반식(IV)의 화합물을 HCl 가스로 포화시킨 메탄올중에 첨가 반응하여 광학적으로 순수한 (R)-form 구조의 일반식(Ib')의 침전물을 분리하여 제조하고, 이어서 상기의 침전물을 여과하고 남은 여과액을 감압 농축하여 실리카겔 컬럼크로마토 그래피(톨루엔 : 에틸아세테이트=4 : 1)하여 광학적으로 순수한 (S)-form 구조의 일반식(Ia')의 화합물을 분리하는 것을 특징으로 하는 제조방법.The compound of formula (IV) was added and reacted in methanol saturated with HCl gas to prepare a precipitate of formula (Ib ') having an optically pure (R) -form structure, and then the precipitate was filtered and left Concentrating the filtrate under reduced pressure and silica gel column chromatography (toluene: ethyl acetate = 4: 1) to separate the compound of the general formula (Ia ') of the optically pure (S) -form structure. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019930024602A 1993-11-18 1993-11-18 Separation method of diastereomer of asymmetric 3-methoxymethyl cephalosporin derivative KR970004048B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1019930024602A KR970004048B1 (en) 1993-11-18 1993-11-18 Separation method of diastereomer of asymmetric 3-methoxymethyl cephalosporin derivative

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
KR1019930024602A KR970004048B1 (en) 1993-11-18 1993-11-18 Separation method of diastereomer of asymmetric 3-methoxymethyl cephalosporin derivative

Publications (2)

Publication Number Publication Date
KR950014123A true KR950014123A (en) 1995-06-15
KR970004048B1 KR970004048B1 (en) 1997-03-24

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