YU48940B - Asimetrična sinteza (-)6-hlor-4-ciklopropiletinil-4-trifluorometil-1,4-dihidro-2h-3,1-benzoksazin-2-ona - Google Patents

Asimetrična sinteza (-)6-hlor-4-ciklopropiletinil-4-trifluorometil-1,4-dihidro-2h-3,1-benzoksazin-2-ona

Info

Publication number
YU48940B
YU48940B YU31496A YU31496A YU48940B YU 48940 B YU48940 B YU 48940B YU 31496 A YU31496 A YU 31496A YU 31496 A YU31496 A YU 31496A YU 48940 B YU48940 B YU 48940B
Authority
YU
Yugoslavia
Prior art keywords
butyllithium
excess
asymmetric synthesis
benzoxazin
ethynyl
Prior art date
Application number
YU31496A
Other languages
English (en)
Other versions
YU31496A (sh
Inventor
Andrew S. Thompson
Edward G. Corley
Edward J.J. Grabowski
Nobuyoshi Yasuda
Original Assignee
Merck & Co.Inc.
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 Merck & Co.Inc. filed Critical Merck & Co.Inc.
Publication of YU31496A publication Critical patent/YU31496A/sh
Publication of YU48940B publication Critical patent/YU48940B/sh

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
    • C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
    • C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D265/18—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/68—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings and hydroxy groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C215/70—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings and hydroxy groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with rings other than six-membered aromatic rings being part of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
    • C07C217/58—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

Postupak za asimetričnu sitezu hiralnog jedinjenja, strukture: gde je P amino zaštitna grupa, naznačen ti me, što obuhvata stupnjeve: a) obezbeđivanje smeše sa viškom (1R,2D)-N-supstituisanog norefedrina sa stukturom; gde je R C 1-4 alkil ili -NR2 obrazuje pirolidinil ili piperidinil; sa ukupnim viškom cikopropilacetilena i viškom litijumskog agensa, koji je odabran od n-butillitijuma, sek-butillitijuma ili terc-butillitijuma, na temperaturi između -78В°C i 10В°C, u neprotonskom rastvaraču; b) mešanje sa smešom iz stupnja (a), jednog ekvivalenta reaktanta strukture: gde je P, kao što je prethodno definisan, a održavajući nastalu reakcionu smešu na temperaturi između -78В°C i -20В°C; i c) gašenje dodavanjem izvora protona kako bi se dobilo željeno jedinjenje. Prijava sadrži još 1 nezavisan i 9 zavisnih zahteva.
YU31496A 1995-05-25 1996-05-24 Asimetrična sinteza (-)6-hlor-4-ciklopropiletinil-4-trifluorometil-1,4-dihidro-2h-3,1-benzoksazin-2-ona YU48940B (sh)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US08/450,330 US5633405A (en) 1995-05-25 1995-05-25 Asymmetric synthesis of (-)-6-chloro-4-cyclopropyl-ethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxanzin-2-one

Publications (2)

Publication Number Publication Date
YU31496A YU31496A (sh) 1998-11-05
YU48940B true YU48940B (sh) 2002-12-10

Family

ID=23787667

Family Applications (1)

Application Number Title Priority Date Filing Date
YU31496A YU48940B (sh) 1995-05-25 1996-05-24 Asimetrična sinteza (-)6-hlor-4-ciklopropiletinil-4-trifluorometil-1,4-dihidro-2h-3,1-benzoksazin-2-ona

Country Status (26)

Country Link
US (2) US5633405A (sh)
EP (1) EP0828703B1 (sh)
JP (1) JP2839717B2 (sh)
KR (1) KR100399511B1 (sh)
CN (1) CN1119319C (sh)
AR (1) AR002997A1 (sh)
AT (1) ATE196463T1 (sh)
AU (1) AU709273B2 (sh)
BR (1) BR9608839A (sh)
CA (1) CA2220389C (sh)
CZ (1) CZ292848B6 (sh)
DE (1) DE69610422T2 (sh)
DK (1) DK0828703T3 (sh)
EA (1) EA000107B1 (sh)
ES (1) ES2151666T3 (sh)
GR (1) GR3034897T3 (sh)
HR (1) HRP960233B1 (sh)
HU (1) HU223565B1 (sh)
MX (1) MX199501B (sh)
NZ (1) NZ308824A (sh)
PT (1) PT828703E (sh)
SK (1) SK282412B6 (sh)
TW (1) TW402581B (sh)
UA (1) UA56137C2 (sh)
WO (1) WO1996037457A1 (sh)
YU (1) YU48940B (sh)

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CA2285000A1 (en) * 1997-04-07 1998-10-15 Dupont Pharmaceuticals Company Asymmetric synthesis of benzoxazinones via new intermediates
AR011731A1 (es) * 1997-05-16 2000-08-30 Merck & Co Inc Un proceso de reaccion de adicion enantioselectiva eficiente utilizando un reactivo de organozinc.
WO1999007657A1 (en) * 1997-08-06 1999-02-18 Merck & Co., Inc. Efficient synthesis of cyclopropylacetylene
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WO1999048848A1 (en) * 1998-03-24 1999-09-30 Great Lakes Chemical Corporation Method to reduce the amount of phosphorus oxyhalides and dihalogenated pentenes in 1,1-dihalo-1-cyclopropylethanes
CO5070643A1 (es) * 1998-05-27 2001-08-28 Merck & Co Inc Formulacion en tabletas comprimidas
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GB2355724A (en) 1999-10-28 2001-05-02 Merck & Co Inc Synthesis of cyclopropylacetylene from propiolic acid (2-propynoic acid)
WO2004087628A1 (fr) * 2003-04-04 2004-10-14 Shanghai Institute Of Organic Chemistry, Chinese Academy Of Sciences Ligand amino-alcool et son utilisation dans la preparation d'alcools tertiaires propargyliques et d'amines tertiaires par le biais d'une reaction d'addition eniantioselective
CN1331601C (zh) * 2003-05-16 2007-08-15 中国科学院上海有机化学研究所 手性氨基醇配体应用于端炔对含氟烷基芳基酮的不对称加成的方法
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US8604189B2 (en) * 2008-05-30 2013-12-10 Emcure Pharmaceuticals Limited Process for the preparation of Efavirenz
WO2010115639A1 (en) 2009-04-09 2010-10-14 Lonza Ltd Process for the synthesis of a propargylic alcohol
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CN101844990B (zh) * 2010-05-27 2013-03-20 浙江沙星医药化工有限公司 中间体4-氯-2-(三氟乙酰基)苯胺盐酸盐水合物的合成方法
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CN102617370B (zh) * 2012-03-05 2014-06-04 浙江江北药业有限公司 (S)-5-氯-α-(环丙乙炔基)-2-(((4-甲氧基苯基)甲基)氨基)-α-(三氟甲基)苯甲醇的制备方法
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Also Published As

Publication number Publication date
DE69610422T2 (de) 2001-04-19
ATE196463T1 (de) 2000-10-15
CA2220389A1 (en) 1996-11-28
US5698741A (en) 1997-12-16
KR19990021899A (ko) 1999-03-25
SK156997A3 (en) 1998-09-09
EA199700426A1 (ru) 1998-06-25
TW402581B (en) 2000-08-21
UA56137C2 (uk) 2003-05-15
CN1119319C (zh) 2003-08-27
CN1185146A (zh) 1998-06-17
PT828703E (pt) 2001-01-31
JP2839717B2 (ja) 1998-12-16
BR9608839A (pt) 1999-06-08
HRP960233B1 (en) 2001-08-31
EP0828703B1 (en) 2000-09-20
HUP9802566A3 (en) 2001-01-29
GR3034897T3 (en) 2001-02-28
YU31496A (sh) 1998-11-05
HUP9802566A2 (hu) 1999-06-28
NZ308824A (en) 1998-11-25
US5633405A (en) 1997-05-27
ES2151666T3 (es) 2001-01-01
CZ292848B6 (cs) 2003-12-17
DE69610422D1 (de) 2000-10-26
AU5866796A (en) 1996-12-11
MX199501B (es) 2000-11-10
DK0828703T3 (da) 2000-11-20
MX9709064A (es) 1998-03-31
KR100399511B1 (ko) 2003-12-31
HRP960233A2 (en) 1997-08-31
AU709273B2 (en) 1999-08-26
EA000107B1 (ru) 1998-08-27
EP0828703A1 (en) 1998-03-18
JPH10506642A (ja) 1998-06-30
WO1996037457A1 (en) 1996-11-28
SK282412B6 (sk) 2002-01-07
HU223565B1 (hu) 2004-09-28
CZ370997A3 (cs) 1998-04-15
CA2220389C (en) 2005-12-06
AR002997A1 (es) 1998-05-27

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