ZA200406589B - Process for the preparation of 2-ethoxy-3-Ä4-(2-(methane-sulphonyloxyphenylüethoxyphenylÜpropanoic acid. - Google Patents
Process for the preparation of 2-ethoxy-3-Ä4-(2-(methane-sulphonyloxyphenylüethoxyphenylÜpropanoic acid. Download PDFInfo
- Publication number
- ZA200406589B ZA200406589B ZA200406589A ZA200406589A ZA200406589B ZA 200406589 B ZA200406589 B ZA 200406589B ZA 200406589 A ZA200406589 A ZA 200406589A ZA 200406589 A ZA200406589 A ZA 200406589A ZA 200406589 B ZA200406589 B ZA 200406589B
- Authority
- ZA
- South Africa
- Prior art keywords
- compound
- formula
- group
- acid
- protecting group
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 26
- 239000002253 acid Substances 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- 125000006239 protecting group Chemical group 0.000 claims abstract description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000003085 diluting agent Substances 0.000 claims abstract description 6
- 239000002585 base Substances 0.000 claims description 10
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- -1 phenylsulfonyloxy group Chemical group 0.000 claims description 6
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical group 0.000 claims description 2
- 150000004679 hydroxides Chemical class 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 5
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 5
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 206010022489 Insulin Resistance Diseases 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical group [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- BQHDGPXFPFAVOA-UHFFFAOYSA-N 3-(4-methylsulfonyloxyphenyl)propane-1-sulfonic acid Chemical compound CS(=O)(=O)OC1=CC=C(CCCS(O)(=O)=O)C=C1 BQHDGPXFPFAVOA-UHFFFAOYSA-N 0.000 description 2
- 201000001320 Atherosclerosis Diseases 0.000 description 2
- 208000032928 Dyslipidaemia Diseases 0.000 description 2
- 108010010234 HDL Lipoproteins Proteins 0.000 description 2
- 102000015779 HDL Lipoproteins Human genes 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 108010062497 VLDL Lipoproteins Proteins 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229940011051 isopropyl acetate Drugs 0.000 description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- CXGTZJYQWSUFET-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-(4-methylsulfonyloxyphenyl)ethoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCC1=CC=C(OS(C)(=O)=O)C=C1 CXGTZJYQWSUFET-UHFFFAOYSA-N 0.000 description 1
- 206010060378 Hyperinsulinaemia Diseases 0.000 description 1
- 208000031773 Insulin resistance syndrome Diseases 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 108090001030 Lipoproteins Proteins 0.000 description 1
- 102000004895 Lipoproteins Human genes 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 208000037849 arterial hypertension Diseases 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- NEJJCKFYYBEQRQ-LBPRGKRZSA-N ethyl (2s)-2-ethoxy-3-(4-hydroxyphenyl)propanoate Chemical compound CCOC(=O)[C@@H](OCC)CC1=CC=C(O)C=C1 NEJJCKFYYBEQRQ-LBPRGKRZSA-N 0.000 description 1
- 230000020764 fibrinolysis Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000035879 hyperinsulinaemia Effects 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 238000003408 phase transfer catalysis Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 108091008012 small dense LDL Proteins 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- CXGTZJYQWSUFET-IBGZPJMESA-N tesaglitazar Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OCCC1=CC=C(OS(C)(=O)=O)C=C1 CXGTZJYQWSUFET-IBGZPJMESA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000009278 visceral effect Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
- C07C303/30—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reactions not involving the formation of esterified sulfo groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
- C07C309/66—Methanesulfonates
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0201005A SE0201005D0 (sv) | 2002-04-02 | 2002-04-02 | New Process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200406589B true ZA200406589B (en) | 2005-09-21 |
Family
ID=20287470
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200406589A ZA200406589B (en) | 2002-04-02 | 2004-08-18 | Process for the preparation of 2-ethoxy-3-Ä4-(2-(methane-sulphonyloxyphenylüethoxyphenylÜpropanoic acid. |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US20050215808A1 (sv) |
| EP (1) | EP1492764B1 (sv) |
| JP (1) | JP2005521725A (sv) |
| KR (1) | KR20050002918A (sv) |
| CN (1) | CN1285571C (sv) |
| AT (1) | ATE331704T1 (sv) |
| AU (1) | AU2003226523A1 (sv) |
| BR (1) | BR0308297A (sv) |
| CA (1) | CA2478650A1 (sv) |
| DE (1) | DE60306506T2 (sv) |
| ES (1) | ES2266842T3 (sv) |
| HK (1) | HK1071353A1 (sv) |
| IL (1) | IL164334A0 (sv) |
| MX (1) | MXPA04009686A (sv) |
| NO (1) | NO20044045L (sv) |
| NZ (1) | NZ534989A (sv) |
| SE (1) | SE0201005D0 (sv) |
| WO (1) | WO2003082812A2 (sv) |
| ZA (1) | ZA200406589B (sv) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9801992D0 (sv) * | 1998-06-04 | 1998-06-04 | Astra Ab | New 3-aryl-2-hydroxypropionic acid derivative I |
| US6358850B1 (en) * | 1999-12-23 | 2002-03-19 | International Business Machines Corporation | Slurry-less chemical-mechanical polishing of oxide materials |
-
2002
- 2002-04-02 SE SE0201005A patent/SE0201005D0/sv unknown
-
2003
- 2003-03-28 CA CA002478650A patent/CA2478650A1/en not_active Abandoned
- 2003-03-28 IL IL16433403A patent/IL164334A0/xx unknown
- 2003-03-28 US US10/509,654 patent/US20050215808A1/en not_active Abandoned
- 2003-03-28 MX MXPA04009686A patent/MXPA04009686A/es not_active Application Discontinuation
- 2003-03-28 KR KR10-2004-7015590A patent/KR20050002918A/ko not_active Application Discontinuation
- 2003-03-28 DE DE60306506T patent/DE60306506T2/de not_active Expired - Fee Related
- 2003-03-28 CN CNB038076853A patent/CN1285571C/zh not_active Expired - Fee Related
- 2003-03-28 WO PCT/GB2003/001395 patent/WO2003082812A2/en active IP Right Grant
- 2003-03-28 AU AU2003226523A patent/AU2003226523A1/en not_active Abandoned
- 2003-03-28 ES ES03745340T patent/ES2266842T3/es not_active Expired - Lifetime
- 2003-03-28 NZ NZ534989A patent/NZ534989A/en unknown
- 2003-03-28 BR BR0308297-0A patent/BR0308297A/pt not_active IP Right Cessation
- 2003-03-28 JP JP2003580280A patent/JP2005521725A/ja not_active Withdrawn
- 2003-03-28 AT AT03745340T patent/ATE331704T1/de not_active IP Right Cessation
- 2003-03-28 EP EP03745340A patent/EP1492764B1/en not_active Expired - Lifetime
-
2004
- 2004-08-18 ZA ZA200406589A patent/ZA200406589B/en unknown
- 2004-09-24 NO NO20044045A patent/NO20044045L/no unknown
-
2005
- 2005-05-13 HK HK05104064A patent/HK1071353A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE60306506D1 (de) | 2006-08-10 |
| CN1285571C (zh) | 2006-11-22 |
| EP1492764A2 (en) | 2005-01-05 |
| EP1492764B1 (en) | 2006-06-28 |
| SE0201005D0 (sv) | 2002-04-02 |
| KR20050002918A (ko) | 2005-01-10 |
| WO2003082812A3 (en) | 2004-01-08 |
| JP2005521725A (ja) | 2005-07-21 |
| CA2478650A1 (en) | 2003-10-09 |
| AU2003226523A1 (en) | 2003-10-13 |
| WO2003082812A2 (en) | 2003-10-09 |
| ATE331704T1 (de) | 2006-07-15 |
| DE60306506T2 (de) | 2007-01-18 |
| NZ534989A (en) | 2006-04-28 |
| HK1071353A1 (en) | 2005-07-15 |
| IL164334A0 (en) | 2005-12-18 |
| BR0308297A (pt) | 2004-12-28 |
| MXPA04009686A (es) | 2005-01-11 |
| ES2266842T3 (es) | 2007-03-01 |
| NO20044045L (no) | 2004-10-18 |
| CN1646487A (zh) | 2005-07-27 |
| US20050215808A1 (en) | 2005-09-29 |
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