KR970065505A - (2R, 3S) -? - phenylisoserine derivative - Google Patents

(2R, 3S) -? - phenylisoserine derivative Download PDF

Info

Publication number
KR970065505A
KR970065505A KR1019960007304A KR19960007304A KR970065505A KR 970065505 A KR970065505 A KR 970065505A KR 1019960007304 A KR1019960007304 A KR 1019960007304A KR 19960007304 A KR19960007304 A KR 19960007304A KR 970065505 A KR970065505 A KR 970065505A
Authority
KR
South Korea
Prior art keywords
compound
formula
acid
cyanide
process according
Prior art date
Application number
KR1019960007304A
Other languages
Korean (ko)
Other versions
KR100225534B1 (en
Inventor
김완주
이관순
채기병
김경수
문영호
김남두
이광옥
하태희
Original Assignee
정지석
한미약품공업 주식회사
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 정지석, 한미약품공업 주식회사 filed Critical 정지석
Priority to KR1019960007304A priority Critical patent/KR100225534B1/en
Priority to PCT/KR1997/000041 priority patent/WO1997034864A1/en
Publication of KR970065505A publication Critical patent/KR970065505A/en
Application granted granted Critical
Publication of KR100225534B1 publication Critical patent/KR100225534B1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/30—Preparation of optical isomers
    • C07C227/32—Preparation of optical isomers by stereospecific synthesis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

본 발명은 탁솔을 합성하는데 중간체로서 유용한 하기 구조식 (Ⅰ)의 (2R,3S)-β-페닐이소세린 유도체의 새로운 입체선택적 제조방법에 관한 것이다.The present invention relates to a novel stereoselective preparation of (2R, 3S) -? - phenylisoserine derivatives of the following structural formula (I) useful as intermediates in the synthesis of taxol.

상기 식에서, R1은 수소, 벤조일 또는 t-부톡시카르보닐을 나타내고, R2는 수소, C1-C4알킬, C1-C4알케닐, C1-C4알키닐 또는 벤질을 나타낸다.Wherein R 1 represents hydrogen, benzoyl or t-butoxycarbonyl and R 2 represents hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkenyl, C 1 -C 4 alkynyl or benzyl .

Description

(2R,3S)-β-페닐이소세린 유도체의 입체선택적 제조방법(2R, 3S) -? - phenylisoserine derivative

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is a trivial issue, I did not include the contents of the text.

Claims (14)

하기 구조식 (11) 화합물을 산촉매 존재하에 수첨반응시켜 하기 구조식 (12) 화합물을 제조한 다음, 알콜 존재 또는 부재하에 가수분해하여 하기 구조식 (13) 화합물을 제조하고 이를 탈보호기화시킴을 특징으로 하여 하기 구조식 (1)의 화합물을 제조하는 방법.The compound of formula (12) is prepared by subjecting a compound of the following formula (11) to hydrogenation in the presence of an acid catalyst, followed by hydrolysis in the presence or absence of an alcohol to prepare a compound of the formula (13) A process for preparing a compound of formula (1) 상기 식에서, R1은 수소, 벤조일 또는 t-부톡시카르보닐을 나타내고, R2는 수소, C1-C4알킬, C1-C4알케닐, C1-C4알키닐 또는 벤질을 나타내며, R3는 수소 또는 트리메틸실릴을 나타낸다.Wherein R 1 represents hydrogen, benzoyl or t-butoxycarbonyl, R 2 represents hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkenyl, C 1 -C 4 alkynyl or benzyl, , And R 3 represents hydrogen or trimethylsilyl. 제1항에 있어서, 구조식 (12) 화합물 제조시 사용되는 산촉매가 염산, 진한황산, 및 질산 중에서 선택된 1종 이상인 방법.The method according to claim 1, wherein the acid catalyst used in preparing the compound of formula (12) is at least one selected from hydrochloric acid, concentrated sulfuric acid, and nitric acid. 제1항에 있어서, 구조식 (13) 화합물 제조시의 가수분해 공정이 진한염산 및 아세트산의 혼합용액 중에서 수행되는 방법.The method according to claim 1, wherein the hydrolysis step in the preparation of the compound of formula (13) is carried out in a mixed solution of concentrated hydrochloric acid and acetic acid. 제3항에 있어서, 진한 염산 및 아세트산의 혼합비율이 부피로 2:1~1:2인 방법.The method according to claim 3, wherein the mixing ratio of concentrated hydrochloric acid and acetic acid is 2: 1 to 1: 2 by volume. 제1항 또는 3항에 있어서, 알콜이 C1-C4알칸올, C1-C4알케닐알콜, C1-C4알키닐알콜 및 벤질알콜 중에서 선택된 1종인 방법.The process according to claim 1 or 3, wherein the alcohol is one selected from the group consisting of C 1 -C 4 alkanols, C 1 -C 4 alkenyl alcohols, C 1 -C 4 alkynyl alcohols and benzyl alcohols. 제1항에 있어서, 탈보호기화 공정이 Pd/C및 암모늄포르메이트 존재하에 수행되거나 Pd/C 및 수소가스(g)존재하에 수행되는 방법.The process according to claim 1, wherein the deprotection is carried out in the presence of Pd / C and ammonium formate or in the presence of Pd / C and hydrogen gas (g). 제1항에 있어서, 탈보호기화 공정을 수행한 후 R1이 수소인 구조식 (1)의 화합물을 벤조일클로라이드 또는 디-t-부틸-디카보네이트와 반응시켜 R1이 벤조일 또는 t-부톡시카르보닐인 구조식 (1)의 화합물을 제조하는 방법.According to claim 1, wherein after performing a deprotection gasification process R 1 is a compound of the formula (1) a hydrogen chloride or di -t- butyl-R 1 is benzoyl or reacted with di-t- butoxycarbonylamino carbonate 0.0 > (1) < / RTI > 제1항에 있어서, 구조식 (11) 화합물이 하기 구조식 (10) 화합물을 시안첨가반응시켜 제조된 것인 방법.The method according to claim 1, wherein the compound of formula (11) is prepared by subjecting a compound of formula (10) 제8항에 있어서, 시안첨가반응을 루이스산 및 시안화물 존재하에 수행하는 방법.9. The process according to claim 8, wherein the cyanation reaction is carried out in the presence of a Lewis acid and a cyanide. 제9항에 있어서, 루이스산이 무수 브롬화마그네슘, 사염화티타늄 및 사염화주석 중에서 선택된 1종인 방법.The process according to claim 9, wherein the Lewis acid is one selected from the group consisting of magnesium bromide anhydride, titanium tetrachloride and tin tetrachloride. 제9항에 있어서, 시안화물이 트리메틸실릴시안, 소듐시아나이드 및 포타슘시아나이드 중에서 선택된 1종인 방법.10. The process of claim 9, wherein the cyanide is one selected from the group consisting of trimethylsilyl cyanide, sodium cyanide, and potassium cyanide. 제8항에 있어서, 구조식 (10) 화합물이 하기 구조식 (4)의 화합물에 벤질할라이드를 반응시켜 구조식 (8) 화합물을 제조하고 이를 환원시켜 구조식 (9) 화합물을 제조한 다음, 스완산화반응을 수행하여 제조된 것인 방법.The method of claim 8, wherein the compound of formula (10) is reacted with a benzyl halide to a compound of formula (4) to produce a compound of formula (8) ≪ / RTI > 제12항에 있어서, 구조식 (8) 화합물을 유기용매 중에서 리튬알루미늄하이드리드로 환원시켜 구조식 (9)의 화합물을 제조하는 방법.13. The method of claim 12, wherein the compound of formula (8) is reduced with lithium aluminum hydride in an organic solvent to produce the compound of formula (9). 제13항에 있어서, 유기용매가 테트라하이드로푸란, 톨루엔, 디에틸에테르, 메틸렌클로라이드, 벤젠 및 크실렌 중에서 선택된 1종 이상인 방법.14. The process according to claim 13, wherein the organic solvent is at least one selected from the group consisting of tetrahydrofuran, toluene, diethyl ether, methylene chloride, benzene and xylene. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: It is disclosed by the contents of the first application.
KR1019960007304A 1996-03-19 1996-03-19 Stereospecific process for preparing (2r,3s)-beta--phenylisoserine KR100225534B1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
KR1019960007304A KR100225534B1 (en) 1996-03-19 1996-03-19 Stereospecific process for preparing (2r,3s)-beta--phenylisoserine
PCT/KR1997/000041 WO1997034864A1 (en) 1996-03-19 1997-03-19 STEREOSELECTIVE PROCESS FOR PREPARATION OF (2R,3S)-β-PHENYLISOSERINE DERIVATIVE

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
KR1019960007304A KR100225534B1 (en) 1996-03-19 1996-03-19 Stereospecific process for preparing (2r,3s)-beta--phenylisoserine

Publications (2)

Publication Number Publication Date
KR970065505A true KR970065505A (en) 1997-10-13
KR100225534B1 KR100225534B1 (en) 1999-10-15

Family

ID=19453377

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019960007304A KR100225534B1 (en) 1996-03-19 1996-03-19 Stereospecific process for preparing (2r,3s)-beta--phenylisoserine

Country Status (2)

Country Link
KR (1) KR100225534B1 (en)
WO (1) WO1997034864A1 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111606824B (en) * 2020-06-24 2023-03-14 东北师范大学 Beta-amino nitrile compound and preparation method thereof

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2023645C (en) * 1989-08-23 2002-03-26 Jean-Noel Denis Process for the enantioselective preparation of phenylisoserin derivatives
US5294737A (en) * 1992-02-27 1994-03-15 The Research Foundation State University Of New York Process for the production of chiral hydroxy-β-lactams and hydroxyamino acids derived therefrom
FR2703353B1 (en) * 1993-03-29 1995-05-05 Rhone Poulenc Rorer Sa Process for the preparation of beta-phenylisoserine derivatives.

Also Published As

Publication number Publication date
KR100225534B1 (en) 1999-10-15
WO1997034864A1 (en) 1997-09-25

Similar Documents

Publication Publication Date Title
Walker The functional group selectivity of complex hydride reducing agents
Ito et al. Practical zirconium-mediated deprotective method of allyl groups
Bajwa et al. Deprotection of N-tosylated indoles and related structures using cesium carbonate
KR960034176A (en) Process for preparing ε-caprolactam and ε-caprolactam precursor
Kaino et al. Stereospecific cyclization of vinyl ether alcohols. Facile synthesis of (-)-lardolure
CN110305010B (en) Preparation method of 2, 5-dimethylphenylacetic acid
Merino et al. Lewis acid stereocontrolled additions of a silyl ketene acetal to 2, 3-di-O-isopropylidene-d-glyceraldehyde nitrones. Synthesis of l-isoxazolidinyl nucleosides
KR970065505A (en) (2R, 3S) -? - phenylisoserine derivative
Yakura et al. Catalytic hypervalent iodine oxidation of p-dialkoxybenzenes to p-quinones using 4-iodophenoxyacetic acid and Oxone®
Murakami et al. A facile synthesis of 1, 5-dienes and β, γ-unsaturated nitriles via trityl perchlorate-catalyzed allylation
Spino et al. Highly stereoselective double michael cyclization of 1-phenylsulfinyl and sulfonyl analogues of the nazarov reagent
JPH0428248B2 (en)
Ohshima et al. Manganese (III)-based oxidative free-radical reaction of α-allyl-β-keto ester with molecular oxygen
Evans et al. Novel approach to lactams via (triisopropylsilyl) azidohydrin formation and photoinduced Schmidt rearrangement
AU666729B2 (en) Process for preparing tetronic acid alkyl esters
JP2503576B2 (en) Process for producing racemic-trans primary chrysanthemic acids
Greene et al. A synthesis of. beta.-methylene-. gamma.-butyrolactones.
Das et al. Vanadium (III) Chloride (VCl3): Efficient Reagent for the Introduction of Tetrahydrofuran‐Based Acetal Protecting Groups for Alcohols
Das et al. An efficient and facile hydroiodination of alkenes and alkynes using polymethylhydrosiloxane–iodine system
KR950005791A (en) Method for preparing carboxylic ester-derivative and 4-fluorobiphenyl derivative used in the method
Salomon Bis-chlorodibutyltin oxide as a new reagent for a mild, versatile and regioselective ring-opening of epoxides
CN114920633B (en) Synthesis process of aldehyde ketone compound
JPH0841065A (en) Production of 1-azabicyclo(3.3.0)octane derivative
US7026504B2 (en) Process for preparing alkyladamantyl esters and compositions
KR960029307A (en) Propylene Glycol Monoalkyl Ether Ester Compounds, and Methods for Making the Compounds

Legal Events

Date Code Title Description
A201 Request for examination
E801 Decision on dismissal of amendment
E902 Notification of reason for refusal
E701 Decision to grant or registration of patent right
GRNT Written decision to grant
FPAY Annual fee payment

Payment date: 20100308

Year of fee payment: 12

LAPS Lapse due to unpaid annual fee