CA2163062C - Process for preparing n-protected amino acid alpha-halomethyl ketones and alcohols from n-protected amino acid esters - Google Patents

Process for preparing n-protected amino acid alpha-halomethyl ketones and alcohols from n-protected amino acid esters

Info

Publication number
CA2163062C
CA2163062C CA002163062A CA2163062A CA2163062C CA 2163062 C CA2163062 C CA 2163062C CA 002163062 A CA002163062 A CA 002163062A CA 2163062 A CA2163062 A CA 2163062A CA 2163062 C CA2163062 C CA 2163062C
Authority
CA
Canada
Prior art keywords
compound
formula
xiii
lower alkyl
solution
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.)
Expired - Fee Related
Application number
CA002163062A
Other languages
English (en)
French (fr)
Other versions
CA2163062A1 (en
Inventor
Ping Chen
Peter Tai Wah Cheng
Steven H. Spergel
Joel C. Barrish
John K. Thottathil
Robert Zahler
Richard P. Polniaszek
Xuebao Wang
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.)
Bristol Myers Squibb Co
Original Assignee
Bristol Myers Squibb Co
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 Bristol Myers Squibb Co filed Critical Bristol Myers Squibb Co
Publication of CA2163062A1 publication Critical patent/CA2163062A1/en
Application granted granted Critical
Publication of CA2163062C publication Critical patent/CA2163062C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/36—Compounds containing oxirane rings with hydrocarbon radicals, substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/18—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by doubly-bound oxygen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Epoxy Compounds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
CA002163062A 1994-12-13 1995-11-16 Process for preparing n-protected amino acid alpha-halomethyl ketones and alcohols from n-protected amino acid esters Expired - Fee Related CA2163062C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US08/355,373 US5481011A (en) 1994-12-13 1994-12-13 Process for preparing N-protected amino acid α-halomethyl ketones and alcohols from N-protected amino acid esters
US08/355,373 1994-12-13

Publications (2)

Publication Number Publication Date
CA2163062A1 CA2163062A1 (en) 1996-06-14
CA2163062C true CA2163062C (en) 1999-02-09

Family

ID=23397213

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002163062A Expired - Fee Related CA2163062C (en) 1994-12-13 1995-11-16 Process for preparing n-protected amino acid alpha-halomethyl ketones and alcohols from n-protected amino acid esters

Country Status (11)

Country Link
US (1) US5481011A (enExample)
EP (1) EP0719769A2 (enExample)
JP (1) JPH08225557A (enExample)
KR (1) KR960022492A (enExample)
CN (1) CN1132203A (enExample)
AU (1) AU690768B2 (enExample)
CA (1) CA2163062C (enExample)
FI (1) FI955955A7 (enExample)
HU (1) HU215249B (enExample)
IL (1) IL116319A0 (enExample)
TW (1) TW365605B (enExample)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100411856B1 (ko) * 1995-02-03 2004-05-20 카네카 코포레이션 α-할로케톤,α-할로히드린및에폭사이드의제조법
USH1893H (en) * 1996-07-23 2000-10-03 Bristol-Myers Squibb Company Enzymatic reduction method for the preparation of halohydrins
CA2319088A1 (en) * 1998-01-28 1999-08-05 Nippon Kayaku Kabushiki Kaisha Process for producing optically active threo-3-amino-1,2-epoxy compounds
DE60005304T2 (de) * 1999-01-21 2004-06-24 Kaneka Corp. Methode zur reinigung und abtrennung von (2s,3s)- oder (2r,3s)-halohydrinderivaten
CA2361475A1 (en) * 1999-01-28 2000-08-03 Ajinomoto Co., Inc. Process for the preparation of .alpha.-aminoketones
EP1661893A3 (en) * 1999-01-29 2006-06-07 Kaneka Corporation Process for the preparation of threo-1,2-epoxy-3-amino-4-phenylbutane derivatives
US6605732B1 (en) * 1999-05-03 2003-08-12 Aerojet Fine Chemicals Llc Clean, high-yield preparation of S,S and R,S amino acid isosteres
KR100339831B1 (ko) * 1999-08-18 2002-06-07 김태성 신규의 에틸 아지리딘 유도체 및 그 제조방법
KR100708221B1 (ko) * 1999-08-31 2007-04-17 아지노모토 가부시키가이샤 에폭사이드 결정의 제조방법
US6992081B2 (en) 2000-03-23 2006-01-31 Elan Pharmaceuticals, Inc. Compounds to treat Alzheimer's disease
ATE343562T1 (de) 2000-03-23 2006-11-15 Elan Pharm Inc Verbindungen und verfahren zur behandlung der alzheimerschen krankheit
CN1217920C (zh) * 2000-06-30 2005-09-07 艾兰制药公司 治疗早老性痴呆的化合物
EP1666452A2 (en) 2000-06-30 2006-06-07 Elan Pharmaceuticals, Inc. Compounds to treat Alzheimer's disease
US20030096864A1 (en) * 2000-06-30 2003-05-22 Fang Lawrence Y. Compounds to treat alzheimer's disease
US6846813B2 (en) 2000-06-30 2005-01-25 Pharmacia & Upjohn Company Compounds to treat alzheimer's disease
PE20020276A1 (es) 2000-06-30 2002-04-06 Elan Pharm Inc COMPUESTOS DE AMINA SUSTITUIDA COMO INHIBIDORES DE ß-SECRETASA PARA EL TRATAMIENTO DE ALZHEIMER
US7253194B2 (en) * 2000-07-24 2007-08-07 The University Of Queensland Compounds and inhibitors of phospholipases
US7122696B2 (en) * 2000-11-30 2006-10-17 Ajinomoto Co., Inc. Processes for preparation of N-protected-β-amino alcohols and N-protected-β-amino epoxides
KR20020046948A (ko) 2000-12-12 2002-06-21 에가시라 구니오 에폭사이드 결정의 제조방법
AR035960A1 (es) * 2001-04-23 2004-07-28 Elan Pharm Inc Epoxidos sustituidos y procesos para prepararlos
MXPA04000140A (es) * 2001-06-27 2004-06-03 Elan Pharm Inc Derivados de beta-hidroxiamina utiles en el tratamiento de enfermedad de alzheimer.
DE10143742A1 (de) 2001-09-06 2003-03-27 Consortium Elektrochem Ind Verfahren zur Herstellung von alpha-Halogenketonen
GB0417824D0 (en) * 2004-08-11 2004-09-15 Phoenix Chemicals Ltd Process for asymmetric catalytic hydrogenation
KR101299972B1 (ko) * 2011-03-30 2013-08-26 순천향대학교 산학협력단 수소화붕소나트륨을 이용한 (3Ｓ)-3-(ｔｅｒｔ-부톡시카르보닐)아미노-1-클로로-4-페닐-(2Ｓ)-부탄올의 제조방법

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1290787A (enExample) * 1970-03-12 1972-09-27
GB1335317A (en) * 1971-06-23 1973-10-24 Leo Pharm Prod Ltd Cephalosporin esters salts thereof and methods for their pre paration
JPS53124226A (en) * 1977-04-07 1978-10-30 Mitsubishi Gas Chem Co Inc Preparation of polyglycidyl compounds
CA1340588C (en) * 1988-06-13 1999-06-08 Balraj Krishan Handa Amino acid derivatives
DD295369A5 (de) * 1988-10-06 1991-10-31 Tech Hochschule C Schorlemmer Verfahren zur herstellung von substituierten glycidylanilinen
ATE141265T1 (de) * 1992-05-20 1996-08-15 Searle & Co Verfahren zur herstellung von intermediaten in der synthese von retroviralen protease inhibitoren
US5559256A (en) * 1992-07-20 1996-09-24 E. R. Squibb & Sons, Inc. Aminediol protease inhibitors

Also Published As

Publication number Publication date
AU4036095A (en) 1996-06-20
FI955955A0 (fi) 1995-12-12
HUT73644A (en) 1996-09-30
FI955955L (fi) 1996-06-14
EP0719769A3 (enExample) 1996-07-31
TW365605B (en) 1999-08-01
FI955955A7 (fi) 1996-06-14
IL116319A0 (en) 1996-03-31
HU9503544D0 (en) 1996-02-28
KR960022492A (ko) 1996-07-18
US5481011A (en) 1996-01-02
HU215249B (hu) 1998-11-30
CA2163062A1 (en) 1996-06-14
EP0719769A2 (en) 1996-07-03
JPH08225557A (ja) 1996-09-03
AU690768B2 (en) 1998-04-30
CN1132203A (zh) 1996-10-02

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