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WO2009027998A3 - A process for the preparation of alanine-nca (alanine-n-carboxyanhydride) from alanine with tri phosgene - Google Patents

A process for the preparation of alanine-nca (alanine-n-carboxyanhydride) from alanine with tri phosgene Download PDF

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Publication number
WO2009027998A3
WO2009027998A3 PCT/IN2008/000540 IN2008000540W WO2009027998A3 WO 2009027998 A3 WO2009027998 A3 WO 2009027998A3 IN 2008000540 W IN2008000540 W IN 2008000540W WO 2009027998 A3 WO2009027998 A3 WO 2009027998A3
Authority
WO
WIPO (PCT)
Prior art keywords
alanine
nca
preparation
present
carboxyanhydride
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/IN2008/000540
Other languages
French (fr)
Other versions
WO2009027998A2 (en
Inventor
Satyanarayana Kota
Venkateswarlu Tallapaneni
Kali Satya Bhujanga Rao Adibhatla
Chowdary Nannapaneni Venkaiah
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Natco Pharma Ltd
Original Assignee
Natco Pharma Ltd
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 Natco Pharma Ltd filed Critical Natco Pharma Ltd
Publication of WO2009027998A2 publication Critical patent/WO2009027998A2/en
Publication of WO2009027998A3 publication Critical patent/WO2009027998A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D263/44—Two oxygen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

Present invention describes a commercial process for preparation of tyrosine-NCA from alanine (IV) and triphosgene (V) that is economically viable, robust, and scalable linearly without using toxic phosgene gas as shown in the scheme 2.Advantages of Present Invention: 1. In the present process hazardous phosgene is replaced with triphosgene and liberated gases are fed to a scrubber, hence it is safe and environmental friendly. 2. The process is suitable for a commercial preparation. 3. The process produces alanine-NCA of purity of > 99%, chlorides < 0.01% and free alanine <0.01%.
PCT/IN2008/000540 2007-08-27 2008-08-26 A process for the preparation of alanine-nca (alanine-n-carboxyanhydride) from alanine with tri phosgene Ceased WO2009027998A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN1916/CHE/2007 2007-08-27
IN1916CH2007 2007-08-27

Publications (2)

Publication Number Publication Date
WO2009027998A2 WO2009027998A2 (en) 2009-03-05
WO2009027998A3 true WO2009027998A3 (en) 2009-04-16

Family

ID=40289371

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2008/000540 Ceased WO2009027998A2 (en) 2007-08-27 2008-08-26 A process for the preparation of alanine-nca (alanine-n-carboxyanhydride) from alanine with tri phosgene

Country Status (1)

Country Link
WO (1) WO2009027998A2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114634547A (en) * 2022-04-26 2022-06-17 山东济肽生物科技有限公司 A kind of synthesis technology of dipeptide-2

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050276783A1 (en) * 2004-06-10 2005-12-15 Ernest Giralt Lledo Polypeptides with the capacity to entrap drugs and release them in a controlled way

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050276783A1 (en) * 2004-06-10 2005-12-15 Ernest Giralt Lledo Polypeptides with the capacity to entrap drugs and release them in a controlled way

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
DALY ET AL: "The preparation of N-carboxyanhydrides of alpha-amino acids using bis(trichloromethyl)carbonate", TETRAHEDRON LETTERS, vol. 29, no. 46, 1988, pages 5859 - 5862, XP002513256 *
DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; 2001, XP002513257, Database accession no. Reaction ID: 8810648 *
RIVERO ET AL, SYNTHETIC COMMUNICATIONS; ENGLISH, vol. 31, no. 14, 2001, pages 2169 - 2176 *

Also Published As

Publication number Publication date
WO2009027998A2 (en) 2009-03-05

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