WO2008006394A8 - Process for the preparation of optically active (4e)-5- halo-2-alkylpent-4-enoic acids and their ester derivatives - Google Patents

Process for the preparation of optically active (4e)-5- halo-2-alkylpent-4-enoic acids and their ester derivatives

Info

Publication number
WO2008006394A8
WO2008006394A8 PCT/EP2006/006897 EP2006006897W WO2008006394A8 WO 2008006394 A8 WO2008006394 A8 WO 2008006394A8 EP 2006006897 W EP2006006897 W EP 2006006897W WO 2008006394 A8 WO2008006394 A8 WO 2008006394A8
Authority
WO
WIPO (PCT)
Prior art keywords
alkylpent
halo
preparation
optically active
ester derivatives
Prior art date
Application number
PCT/EP2006/006897
Other languages
French (fr)
Other versions
WO2008006394A1 (en
Inventor
Mariano Stivanello
Cristiano Grandini
Ennio Grendele
Alessandro Falchi
Original Assignee
Italiana Sint Spa
Mariano Stivanello
Cristiano Grandini
Ennio Grendele
Alessandro Falchi
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 Italiana Sint Spa, Mariano Stivanello, Cristiano Grandini, Ennio Grendele, Alessandro Falchi filed Critical Italiana Sint Spa
Priority to PCT/EP2006/006897 priority Critical patent/WO2008006394A1/en
Publication of WO2008006394A1 publication Critical patent/WO2008006394A1/en
Publication of WO2008006394A8 publication Critical patent/WO2008006394A8/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D275/06—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to the ring sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/06—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid amides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A process for the preparation of optically active (4E)-5-halo-2-alkylpent-4-enoic acids and their ester derivatives by a stereoselective synthesis which employs camphorsultam as chiral auxiliary is disclosed; in particular methyl (2S, 4E)-5-chloro-2-isopropylpent-4-enoate is prepared, which is a key intermediate in the manufacturing of the new anti-hypertension drug Aliskiren. Furthermore novel N-(5-halo-2-alkylpent-4-enoyl) camphorsultams are provided. A process for the hydrolysis of substituted N-acylcamphorsultams with strong acids is also provided.
PCT/EP2006/006897 2006-07-14 2006-07-14 Process for the preparation of optically active (4e)-5- halo-2-alkylpent-4-enoic acids and their ester derivatives WO2008006394A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/EP2006/006897 WO2008006394A1 (en) 2006-07-14 2006-07-14 Process for the preparation of optically active (4e)-5- halo-2-alkylpent-4-enoic acids and their ester derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/EP2006/006897 WO2008006394A1 (en) 2006-07-14 2006-07-14 Process for the preparation of optically active (4e)-5- halo-2-alkylpent-4-enoic acids and their ester derivatives

Publications (2)

Publication Number Publication Date
WO2008006394A1 WO2008006394A1 (en) 2008-01-17
WO2008006394A8 true WO2008006394A8 (en) 2008-03-20

Family

ID=38335702

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2006/006897 WO2008006394A1 (en) 2006-07-14 2006-07-14 Process for the preparation of optically active (4e)-5- halo-2-alkylpent-4-enoic acids and their ester derivatives

Country Status (1)

Country Link
WO (1) WO2008006394A1 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013118138A1 (en) * 2011-12-13 2013-08-15 Laboratories Ltd Mylan Novel process for the preparation of renin inhibitors

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW509672B (en) * 1998-05-12 2002-11-11 Ono Pharmaceutical Co Novel intermediate compounds and processes for the production of optical active octanoic acid derivatives
AU2003289250A1 (en) * 2002-12-09 2004-06-30 Asahi Glass Company, Limited Processes for producing (4e)-5-chloro-2-isopropyl-4-pentenoic ester and optically active isomer thereof

Also Published As

Publication number Publication date
WO2008006394A1 (en) 2008-01-17

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