JP5001263B2 - ジフェニルアラニン誘導体作製のための不斉水素化 - Google Patents
ジフェニルアラニン誘導体作製のための不斉水素化 Download PDFInfo
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- JP5001263B2 JP5001263B2 JP2008512351A JP2008512351A JP5001263B2 JP 5001263 B2 JP5001263 B2 JP 5001263B2 JP 2008512351 A JP2008512351 A JP 2008512351A JP 2008512351 A JP2008512351 A JP 2008512351A JP 5001263 B2 JP5001263 B2 JP 5001263B2
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- ligand
- alkyl
- phenyl
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- formula
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- 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.)
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- 238000009876 asymmetric hydrogenation reaction Methods 0.000 title claims abstract description 11
- PECGVEGMRUZOML-AWEZNQCLSA-N (2s)-2-amino-3,3-diphenylpropanoic acid Chemical class C=1C=CC=CC=1C([C@H](N)C(O)=O)C1=CC=CC=C1 PECGVEGMRUZOML-AWEZNQCLSA-N 0.000 title abstract description 5
- 238000002360 preparation method Methods 0.000 title abstract description 3
- 238000000034 method Methods 0.000 claims abstract description 29
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- 229910052703 rhodium Inorganic materials 0.000 claims abstract description 8
- 239000010948 rhodium Substances 0.000 claims abstract description 8
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000003446 ligand Substances 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000005610 enamide group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 238000009905 homogeneous catalytic hydrogenation reaction Methods 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- OOLUVSIJOMLOCB-UHFFFAOYSA-N 1633-22-3 Chemical group C1CC(C=C2)=CC=C2CCC2=CC=C1C=C2 OOLUVSIJOMLOCB-UHFFFAOYSA-N 0.000 claims description 2
- -1 3,5-dimethylphenyl Chemical group 0.000 claims description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000002210 biocatalytic effect Effects 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 239000008186 active pharmaceutical agent Substances 0.000 description 5
- GYZZZILPVUYAFJ-UHFFFAOYSA-N phanephos Chemical compound C1CC(C(=C2)P(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=C2CCC2=CC=C1C=C2P(C=1C=CC=CC=1)C1=CC=CC=C1 GYZZZILPVUYAFJ-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- OLKADVDHTQNPFW-UHFFFAOYSA-N methyl 2-acetamido-3,3-diphenylprop-2-enoate Chemical compound C=1C=CC=CC=1C(=C(NC(C)=O)C(=O)OC)C1=CC=CC=C1 OLKADVDHTQNPFW-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 150000001371 alpha-amino acids Chemical class 0.000 description 2
- 235000008206 alpha-amino acids Nutrition 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- 102000004196 processed proteins & peptides Human genes 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- IRZQDMYEJPNDEN-NETXQHHPSA-N (2s)-2-amino-3-phenylbutanoic acid Chemical class OC(=O)[C@@H](N)C(C)C1=CC=CC=C1 IRZQDMYEJPNDEN-NETXQHHPSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 108010029144 Factor IIa Proteins 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229940124158 Protease/peptidase inhibitor Drugs 0.000 description 1
- 101000712605 Theromyzon tessulatum Theromin Proteins 0.000 description 1
- 229940122388 Thrombin inhibitor Drugs 0.000 description 1
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000005248 alkyl aryloxy group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 239000011942 biocatalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 229940088679 drug related substance Drugs 0.000 description 1
- 239000011982 enantioselective catalyst Substances 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000003868 thrombin inhibitor Substances 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68315005P | 2005-05-20 | 2005-05-20 | |
| US60/683,150 | 2005-05-20 | ||
| PCT/US2006/017978 WO2006127273A2 (en) | 2005-05-20 | 2006-05-09 | Asymmetric hydrogenation for the preparation of diphenylalanine derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008540650A JP2008540650A (ja) | 2008-11-20 |
| JP2008540650A5 JP2008540650A5 (enExample) | 2012-05-31 |
| JP5001263B2 true JP5001263B2 (ja) | 2012-08-15 |
Family
ID=37027602
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008512351A Expired - Fee Related JP5001263B2 (ja) | 2005-05-20 | 2006-05-09 | ジフェニルアラニン誘導体作製のための不斉水素化 |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP1885688B1 (enExample) |
| JP (1) | JP5001263B2 (enExample) |
| CN (1) | CN101175715B (enExample) |
| AT (1) | ATE482182T1 (enExample) |
| DE (1) | DE602006017064D1 (enExample) |
| WO (1) | WO2006127273A2 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8680278B2 (en) * | 2007-10-30 | 2014-03-25 | Janssen Pharmaceutica Nv | Enantioselective process for preparing a substituted alkanoic acid |
| JP2023535595A (ja) * | 2020-07-28 | 2023-08-18 | ジャズ ファーマシューティカルズ アイルランド リミテッド | 縮合二環式ｒａｆ阻害剤のキラル合成 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5198548A (en) * | 1992-01-30 | 1993-03-30 | Warner-Lambert Company | Process for the preparation of D(-) and L(+)-3,3-diphenylalanine and D(-) and L(+)-substituted 3,3-diphenylalanines and derivatives thereof |
| US5874629A (en) * | 1996-06-12 | 1999-02-23 | Merck & Co., Inc. | Chiral bisphosphines |
| WO2002057278A1 (en) * | 2001-01-19 | 2002-07-25 | Chirotech Technology Limited | Ligands and their use |
| JP2007537256A (ja) * | 2004-05-11 | 2007-12-20 | メルク エンド カムパニー インコーポレーテッド | Ｎ−スルホン化アミノ酸誘導体調製のためのプロセス |
-
2006
- 2006-05-09 EP EP06770147A patent/EP1885688B1/en not_active Not-in-force
- 2006-05-09 AT AT06770147T patent/ATE482182T1/de not_active IP Right Cessation
- 2006-05-09 WO PCT/US2006/017978 patent/WO2006127273A2/en not_active Ceased
- 2006-05-09 DE DE602006017064T patent/DE602006017064D1/de active Active
- 2006-05-09 CN CN2006800170720A patent/CN101175715B/zh not_active Expired - Fee Related
- 2006-05-09 JP JP2008512351A patent/JP5001263B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2008540650A (ja) | 2008-11-20 |
| CN101175715B (zh) | 2011-04-13 |
| ATE482182T1 (de) | 2010-10-15 |
| WO2006127273A3 (en) | 2007-03-22 |
| DE602006017064D1 (de) | 2010-11-04 |
| EP1885688A2 (en) | 2008-02-13 |
| EP1885688B1 (en) | 2010-09-22 |
| WO2006127273A2 (en) | 2006-11-30 |
| CN101175715A (zh) | 2008-05-07 |
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