AR049879A1 - Proceso para la preparacion de derivados de beta aminoacidos enantiomericamente enriquecidos - Google Patents
Proceso para la preparacion de derivados de beta aminoacidos enantiomericamente enriquecidosInfo
- Publication number
- AR049879A1 AR049879A1 ARP050101320A ARP050101320A AR049879A1 AR 049879 A1 AR049879 A1 AR 049879A1 AR P050101320 A ARP050101320 A AR P050101320A AR P050101320 A ARP050101320 A AR P050101320A AR 049879 A1 AR049879 A1 AR 049879A1
- Authority
- AR
- Argentina
- Prior art keywords
- bis
- diphenylphosphino
- alkyl
- substituted
- benzene
- Prior art date
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
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/16—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions not involving the amino or carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/16—Preparation of optical isomers
- C07C231/18—Preparation of optical isomers by stereospecific synthesis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/55—Acids; Esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Se refiere a un procedimiento para la preparacion eficiente de derivados de beta aminio ácido enantioméricamente enriquecido donde el grupo amino no está protegido. Los productos derivados beta aminoácidos quirales son utiles en la síntesis asimétrica de moléculas biologicamente activas. El procedimiento comprende una hidrogenacion enantioselectiva de una amina no protegida proquiral de ácido acrílico beta amino o el derivado en la presencia del precursor rodio metal complejado con un ligando quiral mono- o bisfosfina. Reivindicacion 1: Un procedimiento para la preparacion de un compuesto de formula estructural (1), enantioméricamente enriquecido en el átomo marcado con un *; donde Z es OR2, SR2, o NR2R3; R1 es alquil C1-8, aril, heteroaril, aril-alquilC1-2, o heteroaril-alquilC1-2; E2 y R3 son cada uno independientemente hidrogeno, alquil C1-8, aril, o aril-alquilC1-2; o R2 y R3 junto con el átomo de nitrogeno al cual ellos están unidos para formar un sistema heterocíclico anular de 4- a 7- miembros que opcionalmente contiene un heteroátomo adicional seleccionado entre O, S, N, NH, y N alquilC1-4, dicho anillo heterocíclico puede estar no sustituido o sustituido con de uno a tres sustituyentes independientemente seleccionados entre oxo, hidroxi, halogeno, alcoxi C1-4, y alquil C1-4 donde el alquil y el alcoxi están no sustituidos o sustituidos con de uno a cinco átomos de fluor; y dicho sistema anular heterocíclico está opcionalmente fusionado con un sistema anular carbocíclico aromático o saturado de 5- a 6- miembros o sistema anular heterocíclico aromático o saturado de 5- a 6- miembros que contiene de uno a tres heteroátomos seleccionados entre O, S, N, NH, y N alquilC1-4, dicho sistema anular fusionado puede estar no sustituido o sustituido con de uno a cuatro sustituyentes seleccionados entre hidroxi, amino, fluor, alquil C1-4, y alcoxi C1-4, donde el alquil y el alcoxi no están sustituidos o están sustituidos con de uno a cinco átomos de fluor; que comprenden el paso de la hidrogenacion en la presencia de hidrogeno gas de una enamina proquiral de formula estructural (2), en un solventes adecuado en la presencia del precursor metal sodio complejado a un ligando quiral mono- o bisfosfina; con las condiciones de que: a) el ligando bisfosfina quiral no es un ligando ferrocenil bisfosfina de formula estructural (3), donde R4 es alquil C1-4 o aril; R5 y R6 son cada uno independientemente alquil C1-6, cicloalquil C5-12, o aril; y R7 es alquilC1-4 o fenil no sustituido; y que b) el ligando quiral bisfosfina no es un ligando seleccionado entre el grupo consistente en: 1,2-bis(anisilfenilfosfino)etano; 1,2-bis(alquilmetilfosfino)etano; 2,3- bis(difenilfosfino)butano; 1,2-bis(difenilfosfino)propano; 2,3-bis(difenilfosfino)-5-norborneno; 2,3-O-isopropiliden-2,3-dihidroxi-1,4-bis-(difenilfosfino)butano; 1-ciclohexil-1,2-bis(difenilfosfino)etano; 1-sustituido-3,4- bis(difenilfosfino)pirrolidina; 2,4-bis(difenilfosfino)pentano; 1,2-bis(fosfolano sustituido)benceno; 1,2-bis(fosfolano sustituido)etano; 1-(fosfolano sustituido)-2-(difenilfosfino)benceno; 1-(bis(3,5-dimetilfenil)fosfino)-2-(fosfolano sustituido)benceno; 1-(fosfolano sustituido)-2-(bis(3,5-di(t-butil)-4-metoxifenil)fosfino)benceno; 1-(fosfolano sustituido)-2-(di-naftalen-1-il-fosfino)benceno; 2,2'-bis(difenilfosfino)-1,1'-binaftil; 2,2'-bis(di-p-tolilfosfino)-1,1'-binaftil; 2,2'- bis(di(3,5-dimetilfenil)fosfino)-1,1'-binaftil; 2,2'-bis(difenilfosfino)-6,6'-dimetil-1,1'-bifenil; ((5,6)(5',6')-bis(metilenedioxi)bifenil-2,2'-diil)(bisdifenilfosfina); ((5,6)(5',6')-bis(metilenedioxi)bifenil-2,2'-diil)(bis(3,5- dimetilfenil)fosfina); ((5,6)(5',6')-bis(metilenedioxi)bifenil-2,2'-diil)(bis(3,5-di(t-butil)fenil)fosfina); ciclohexilanisilmetilfosfina; 1-[1',2-bis(difenilfosfino)ferrocenil]etilamina; 1-[1',2-bis(difenilfosfino)ferrocenil]etil alcohol; 2,2'- bis(difenilfosfino)-1,1'-ciclopentano; y 2,2'-bis(difenilfosfino)-1,1'-(5,5'6,6',7,7'8,8'-octahidrobinaftil.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US55951404P | 2004-04-05 | 2004-04-05 | |
US64669805P | 2005-01-24 | 2005-01-24 |
Publications (1)
Publication Number | Publication Date |
---|---|
AR049879A1 true AR049879A1 (es) | 2006-09-13 |
Family
ID=34964957
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ARP050101320A AR049879A1 (es) | 2004-04-05 | 2005-04-04 | Proceso para la preparacion de derivados de beta aminoacidos enantiomericamente enriquecidos |
Country Status (8)
Country | Link |
---|---|
US (1) | US7495123B2 (es) |
EP (1) | EP1735269A1 (es) |
JP (1) | JP2007531795A (es) |
AR (1) | AR049879A1 (es) |
AU (1) | AU2005230693A1 (es) |
CA (1) | CA2561973A1 (es) |
TW (1) | TW200602293A (es) |
WO (1) | WO2005097733A1 (es) |
Families Citing this family (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AR043515A1 (es) | 2003-03-19 | 2005-08-03 | Merck & Co Inc | Procedimiento para preparar derivados quirales beta aminoacidos mediante hidrogenacion asimetrica |
AR052879A1 (es) * | 2005-01-24 | 2007-04-11 | Merck & Co Inc | Procedimiento para preparar derivados de beta aminoacidos quirales por hidrogenacion asimetrica |
AU2006242542A1 (en) | 2005-04-29 | 2006-11-09 | Wyeth | Process for preparing 3,3-disubstituted oxindoles and thio-oxindoles |
WO2008031750A2 (en) * | 2006-09-15 | 2008-03-20 | F. Hoffmann-La Roche Ag | Process for the preparation of pyrido[2,1-a]isoquinoline derivatives by catalytic asymmetric hydrogenation of an enamine |
JP2011519340A (ja) * | 2007-10-30 | 2011-07-07 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 置換アルカン酸調製のためのエナンチオ選択的プロセスこの米国特許正規出願は、2007年10月30日に提出された米国特許仮出願第61/001,004号、及び2008年2月29日に提出された米国特許仮出願第61/067,842号の権利を主張する。 |
US8334385B2 (en) * | 2007-11-02 | 2012-12-18 | Glenmark Generics Limited | Process for the preparation of R-sitagliptin and its pharmaceutically acceptable salts thereof |
EP2223923A1 (en) | 2009-02-25 | 2010-09-01 | Esteve Química, S.A. | Process for the preparation of a chiral beta aminoacid derivative and intermediates thereof |
IT1395596B1 (it) | 2009-06-30 | 2012-10-16 | Dipharma Francis Srl | Procedimento per la preparazione di sitagliptin |
CZ303113B6 (cs) * | 2010-03-16 | 2012-04-11 | Zentiva, K.S. | Zpusob prípravy sitagliptinu |
WO2011135586A2 (en) | 2010-04-28 | 2011-11-03 | Sun Pharmaceutical Industries Ltd. | Process for the preparation of chiral beta amino carboxamide derivatives |
WO2011151443A1 (en) | 2010-06-04 | 2011-12-08 | Lek Pharmaceuticals D.D. | A NOVEL SYNTHETIC APPROACH TO ß-AMINOBUTYRYL SUBSTITUTED COMPOUNDS |
EP2392575A1 (en) | 2010-06-04 | 2011-12-07 | LEK Pharmaceuticals d.d. | A novel synthetic approach to ß-aminobutyryl substituted compounds |
EP2397141A1 (en) | 2010-06-16 | 2011-12-21 | LEK Pharmaceuticals d.d. | Process for the synthesis of beta-amino acids and derivatives thereof |
EP2508506A1 (en) | 2011-04-08 | 2012-10-10 | LEK Pharmaceuticals d.d. | Preparation of sitagliptin intermediates |
EP2527320A1 (en) | 2011-05-27 | 2012-11-28 | LEK Pharmaceuticals d.d. | Preparation of Sitagliptin Intermediates |
EP2736909B1 (en) | 2011-07-27 | 2017-03-29 | Farma GRS, d.o.o. | Process for the preparation of sitagliptin and its pharmaceutically acceptable salts |
WO2013065066A1 (en) | 2011-11-02 | 2013-05-10 | Cadila Healthcare Limited | Processes for preparing 4-oxo-4-[3-(trifluoromethyl)-5,6- dihydro [l,2,41-triazolo[43-a]pyrazin-7(8h)-yl]-l-(2,4,5- trifluorophenyl)butan-2-amine |
EP2615080A1 (en) | 2012-01-12 | 2013-07-17 | LEK Pharmaceuticals d.d. | Preparation of Optically Pure ß-Amino Acid Type Active Pharmaceutical Ingredients and Intermediates thereof |
EP2674432A1 (en) | 2012-06-14 | 2013-12-18 | LEK Pharmaceuticals d.d. | New synthetic route for the preparation of ß aminobutyryl substituted 5,6,7,8-tetrahydro[1,4]diazolo[4,3-alpha]pyrazin-7-yl compounds |
CA2901591A1 (en) | 2013-03-11 | 2014-10-09 | Rutgers, The State University Of New Jersey | Metallorganocatalysis for asymmetric transformations |
IN2013MU00916A (es) | 2013-03-20 | 2015-06-26 | Cadila Healthcare Ltd | |
EP3159343B1 (en) | 2015-10-22 | 2017-07-19 | F.I.S.- Fabbrica Italiana Sintetici S.p.A. | Improved process for the preparation of triazole and salt thereof |
US10047094B1 (en) | 2017-02-10 | 2018-08-14 | F.I.S.—Fabbrica Italiana Sintetici S.p.A. | Process for the preparation of triazole and salt thereof |
US20220048917A1 (en) * | 2018-12-11 | 2022-02-17 | Council Of Scientific & Industrial Research | Highly efficient process for the preparation of sitagliptin via rhodium catalyzed asymmetric hydrogenation |
WO2020194337A2 (en) * | 2019-03-28 | 2020-10-01 | Council Of Scientific And Industrial Research | A process for the asymmetric synthesis of sitagliptin intermediate |
CN113636950B (zh) | 2020-05-11 | 2023-01-17 | 浙江医药股份有限公司新昌制药厂 | 一种手性4-芳基-β-氨基酸衍生物的制备方法 |
CN114516847B (zh) * | 2022-03-09 | 2024-01-30 | 台州达辰药业有限公司 | 一种西他列汀中间体的制备方法 |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SG42936A1 (en) | 1992-04-02 | 1997-10-17 | Ciba Geigy Ag | Ferrocenyl diphosphines as ligands for homogeneous catalysts |
EP0967015B1 (de) | 1998-06-19 | 2005-01-12 | Degussa AG | Verwendung von Ferrocenylliganden zur katalytischen enantioselektiven Hydrierung |
EP1228034A4 (en) * | 1999-11-10 | 2003-05-07 | Penn State Res Found | CHIRAL PHOSPHINES, AND COMPLEXES THEREOF WITH TRANSITIONAL METALS AND USE OF SUCH COMPLEXES IN ASYMMETRIC REACTIONS |
US6258979B1 (en) | 1999-11-22 | 2001-07-10 | Henri Kagan | Chiral ferrocene phosphines active in asymmetric catalysis |
DE19956414A1 (de) | 1999-11-24 | 2001-06-13 | Aventis Res & Tech Gmbh & Co | Verfahren zur Herstellung von chiralen Aminen durch homogen katalysierte asymmetrische Hydrierung von Enaminen |
AU2002216719A1 (en) | 2000-11-17 | 2002-05-27 | The Penn State Research Foundation | Ortho substituted chiral phosphines and phosphinites and their use in asymmetriccatayltic reactions |
DE10100971A1 (de) | 2001-01-11 | 2002-07-18 | Degussa | Verfahren zur Herstellung enantiomerenangereicherter beta-Aminosäure |
US6808773B2 (en) | 2001-05-24 | 2004-10-26 | Kyodo Printing Co., Ltd. | Shielding base member and method of manufacturing the same |
UA74912C2 (en) | 2001-07-06 | 2006-02-15 | Merck & Co Inc | Beta-aminotetrahydroimidazo-(1,2-a)-pyrazines and tetratriazolo-(4,3-a)-pyrazines as inhibitors of dipeptylpeptidase for the treatment or prevention of diabetes |
EP1386901B1 (en) * | 2002-07-30 | 2015-07-01 | Takasago International Corporation | Method for producing an optically active beta-amino acid |
AR043515A1 (es) * | 2003-03-19 | 2005-08-03 | Merck & Co Inc | Procedimiento para preparar derivados quirales beta aminoacidos mediante hidrogenacion asimetrica |
-
2005
- 2005-04-01 TW TW094110552A patent/TW200602293A/zh unknown
- 2005-04-04 AR ARP050101320A patent/AR049879A1/es unknown
- 2005-04-05 JP JP2007507450A patent/JP2007531795A/ja not_active Withdrawn
- 2005-04-05 WO PCT/US2005/011585 patent/WO2005097733A1/en active Application Filing
- 2005-04-05 AU AU2005230693A patent/AU2005230693A1/en not_active Abandoned
- 2005-04-05 CA CA002561973A patent/CA2561973A1/en not_active Abandoned
- 2005-04-05 US US11/547,183 patent/US7495123B2/en active Active
- 2005-04-05 EP EP05732844A patent/EP1735269A1/en not_active Withdrawn
Also Published As
Publication number | Publication date |
---|---|
WO2005097733A1 (en) | 2005-10-20 |
EP1735269A1 (en) | 2006-12-27 |
TW200602293A (en) | 2006-01-16 |
US7495123B2 (en) | 2009-02-24 |
JP2007531795A (ja) | 2007-11-08 |
AU2005230693A1 (en) | 2005-10-20 |
US20080058522A1 (en) | 2008-03-06 |
CA2561973A1 (en) | 2005-10-20 |
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