CA1132560A - Process for inverting the configuration in optically active compounds and new optically active intermediates required therefor and the salts thereof - Google Patents
Process for inverting the configuration in optically active compounds and new optically active intermediates required therefor and the salts thereofInfo
- Publication number
- CA1132560A CA1132560A CA332,626A CA332626A CA1132560A CA 1132560 A CA1132560 A CA 1132560A CA 332626 A CA332626 A CA 332626A CA 1132560 A CA1132560 A CA 1132560A
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- compound
- formula
- acid
- lower alkyl
- 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
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 89
- 150000003839 salts Chemical class 0.000 title claims abstract description 40
- 238000000034 method Methods 0.000 title claims abstract description 38
- 239000000543 intermediate Substances 0.000 title description 9
- -1 (1-pyrryl)-phenyl Chemical group 0.000 claims abstract description 218
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 114
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 37
- 125000005037 alkyl phenyl group Chemical group 0.000 claims abstract description 16
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims abstract description 13
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims abstract description 13
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims abstract description 8
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims abstract description 7
- 125000004848 alkoxyethyl group Chemical group 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims description 59
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 38
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 33
- 239000001117 sulphuric acid Substances 0.000 claims description 33
- 235000011149 sulphuric acid Nutrition 0.000 claims description 33
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 32
- 239000007858 starting material Substances 0.000 claims description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 18
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 18
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 11
- 231100000252 nontoxic Toxicity 0.000 claims description 11
- 230000003000 nontoxic effect Effects 0.000 claims description 11
- 239000012458 free base Substances 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 230000003301 hydrolyzing effect Effects 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 238000009833 condensation Methods 0.000 claims description 7
- 230000005494 condensation Effects 0.000 claims description 7
- 230000007062 hydrolysis Effects 0.000 claims description 7
- 238000006460 hydrolysis reaction Methods 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 150000001450 anions Chemical class 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 3
- 235000013350 formula milk Nutrition 0.000 claims 27
- 238000011065 in-situ storage Methods 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 1
- 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 1
- 239000000243 solution Substances 0.000 description 44
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- 150000003254 radicals Chemical class 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 125000003545 alkoxy group Chemical group 0.000 description 17
- 230000000875 corresponding effect Effects 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- 229910052799 carbon Inorganic materials 0.000 description 12
- 230000008018 melting Effects 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- 238000007792 addition Methods 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 10
- 235000011007 phosphoric acid Nutrition 0.000 description 10
- 150000001721 carbon Chemical group 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 8
- 125000005115 alkyl carbamoyl group Chemical group 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 125000003282 alkyl amino group Chemical group 0.000 description 7
- 125000005237 alkyleneamino group Chemical group 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 150000004820 halides Chemical class 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 125000004430 oxygen atom Chemical group O* 0.000 description 7
- 125000003396 thiol group Chemical group [H]S* 0.000 description 7
- 125000004414 alkyl thio group Chemical group 0.000 description 6
- 125000005281 alkyl ureido group Chemical group 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 235000011167 hydrochloric acid Nutrition 0.000 description 6
- 229960000443 hydrochloric acid Drugs 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 5
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 125000005236 alkanoylamino group Chemical group 0.000 description 4
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 4
- 125000006383 alkylpyridyl group Chemical group 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 4
- 125000001041 indolyl group Chemical group 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 125000003373 pyrazinyl group Chemical group 0.000 description 4
- 125000005554 pyridyloxy group Chemical group 0.000 description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- AYFVYJQAPQTCCC-UHFFFAOYSA-N THREONINE Chemical compound CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 125000004442 acylamino group Chemical group 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 125000002619 bicyclic group Chemical group 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 229910021653 sulphate ion Inorganic materials 0.000 description 3
- DLNKOYKMWOXYQA-CBAPKCEASA-N (-)-norephedrine Chemical compound C[C@H](N)[C@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-CBAPKCEASA-N 0.000 description 2
- 125000004518 1,2,5-thiadiazol-3-yl group Chemical group S1N=C(C=N1)* 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- AYFVYJQAPQTCCC-HRFVKAFMSA-N L-allothreonine Chemical compound C[C@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-HRFVKAFMSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 238000006640 acetylation reaction Methods 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 125000003302 alkenyloxy group Chemical group 0.000 description 2
- 125000005108 alkenylthio group Chemical group 0.000 description 2
- 125000005133 alkynyloxy group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000001589 carboacyl group Chemical group 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 150000002918 oxazolines Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- ZMRUPTIKESYGQW-UHFFFAOYSA-N propranolol hydrochloride Chemical compound [H+].[Cl-].C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 ZMRUPTIKESYGQW-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 125000003198 secondary alcohol group Chemical group 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 1
- KWGRBVOPPLSCSI-SCZZXKLOSA-N (1r,2r)-2-(methylamino)-1-phenylpropan-1-ol Chemical compound CN[C@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-SCZZXKLOSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- XLHUBROMZOAQMV-UHFFFAOYSA-N 1,4-benzosemiquinone Chemical group [O]C1=CC=C(O)C=C1 XLHUBROMZOAQMV-UHFFFAOYSA-N 0.000 description 1
- NJEIOWSBPCZKTL-UHFFFAOYSA-N 1-(2-chloro-5-methylphenoxy)-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC(C)=CC=C1Cl NJEIOWSBPCZKTL-UHFFFAOYSA-N 0.000 description 1
- HIOSGQZZOJVIJJ-UHFFFAOYSA-N 1-(2-methylphenyl)sulfanyl-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)CSC1=CC=CC=C1C HIOSGQZZOJVIJJ-UHFFFAOYSA-N 0.000 description 1
- KDOYLLNDEQHAAK-UHFFFAOYSA-N 1-(3-chloropyridin-2-yl)oxy-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=NC=CC=C1Cl KDOYLLNDEQHAAK-UHFFFAOYSA-N 0.000 description 1
- FYOGTFROMBUNKU-UHFFFAOYSA-N 1-(propan-2-ylamino)-3-(2-prop-2-ynoxyphenoxy)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1OCC#C FYOGTFROMBUNKU-UHFFFAOYSA-N 0.000 description 1
- DVEVLTYQYJYQIA-UHFFFAOYSA-N 1-(propan-2-ylamino)-3-pyrazin-2-yloxypropan-2-ol Chemical compound CC(C)NCC(O)COC1=CN=CC=N1 DVEVLTYQYJYQIA-UHFFFAOYSA-N 0.000 description 1
- MYJOGYCKRILART-UHFFFAOYSA-N 1-[4-(2-methylsulfanylethoxy)phenoxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound CSCCOC1=CC=C(OCC(O)CNC(C)C)C=C1 MYJOGYCKRILART-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical group CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
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- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
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
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D263/14—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Lasers (AREA)
- Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH8145/78-4 | 1978-07-28 | ||
| CH814578 | 1978-07-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1132560A true CA1132560A (en) | 1982-09-28 |
Family
ID=4335835
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA332,626A Expired CA1132560A (en) | 1978-07-28 | 1979-07-26 | Process for inverting the configuration in optically active compounds and new optically active intermediates required therefor and the salts thereof |
Country Status (10)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5319141A (en) * | 1989-09-25 | 1994-06-07 | Acic (Canada) Inc. | Process of making nadolol |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3125870C2 (de) * | 1980-07-09 | 1994-09-15 | William John Louis | 3-Aminopropoxyphenyl Derivate, ihre Herstellung und sie enthaltende Arzneimittel |
| DE3229046A1 (de) * | 1982-08-04 | 1984-02-16 | Hoechst Ag, 6230 Frankfurt | Verfahren zur umkehrung der konfiguration optisch aktiver verbindungen und optisch aktive zwischenprodukte dieses verfahrens |
| FR2536390B1 (fr) * | 1982-11-22 | 1986-03-21 | Synthelabo | Isomere s du betaxolol, sa preparation et son application en therapeutique |
| JPH0739394B2 (ja) * | 1985-05-30 | 1995-05-01 | 住友化学工業株式会社 | 含窒素複素環化合物およびそれを有効成分として含有する有害生物防除剤 |
| DE3544172A1 (de) * | 1985-12-13 | 1987-06-19 | Lentia Gmbh | Neue kristalline salze von aryloxy-propanolaminen, verfahren zu ihrer herstellung und ihre verwendung |
| US4920134A (en) * | 1987-08-07 | 1990-04-24 | Takeda Chemical Industries, Ltd. | 2-O-pyrimidinyl glycerol derivatives |
| JP2002080435A (ja) * | 2000-06-26 | 2002-03-19 | Kanegafuchi Chem Ind Co Ltd | ３−アミノ−２−ヒドロキシプロピオン酸誘導体の製造法 |
| US7307184B2 (en) * | 2001-05-23 | 2007-12-11 | Kaneka Corporation | Processes for preparing oxazolidinone derivatives of β-hydroxyethlamine compounds and for preparing β-hydroxyethlamine compounds |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE585164C (de) | 1932-06-11 | 1933-09-29 | Helmut Legerlotz Dr | Verfahren zur Umkehrung des Drehungssinnes von optisch aktiven Phenylalkaminen |
| US2446192A (en) * | 1946-01-26 | 1948-08-03 | Merck & Co Inc | Preparation of threonine and derivatives thereof |
| GB1069343A (en) * | 1963-09-10 | 1967-05-17 | Ici Ltd | Propanolamine derivatives |
| GB1136919A (en) * | 1965-06-16 | 1968-12-18 | Ici Ltd | Amines |
| US3994917A (en) * | 1965-10-22 | 1976-11-30 | Eli Lilly And Company | Oxazolinium salt process |
| DE1720005A1 (de) * | 1968-03-01 | 1971-05-19 | Bayer Ag | Verfahren zur Herstellung von Oxazolinen |
| BE790569A (fr) * | 1971-10-27 | 1973-04-26 | Syntex Corp | Agents cardiovasculaires a base de thiazoles |
| HU167760B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1972-10-20 | 1975-12-25 | ||
| HU167262B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1972-12-22 | 1975-09-27 | ||
| CH585693A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1974-02-08 | 1977-03-15 | Ciba Geigy Ag | |
| US4000282A (en) * | 1974-12-16 | 1976-12-28 | Merck & Co., Inc. | 2-(3-tert. butyl or isopropylamino-2-hydroxypropoxy)-3-cyanopyridines |
| US4237304A (en) * | 1978-10-26 | 1980-12-02 | The Dow Chemical Company | Oxazolinium salts and method of preparation |
-
1979
- 1979-07-16 US US06/058,222 patent/US4294966A/en not_active Expired - Lifetime
- 1979-07-23 AT AT79102592T patent/ATE1547T1/de not_active IP Right Cessation
- 1979-07-23 EP EP79102592A patent/EP0007605B1/de not_active Expired
- 1979-07-23 DE DE7979102592T patent/DE2963675D1/de not_active Expired
- 1979-07-24 ES ES482806A patent/ES482806A1/es not_active Expired
- 1979-07-26 AU AU49258/79A patent/AU529335B2/en not_active Ceased
- 1979-07-26 FI FI792337A patent/FI69051C/fi not_active IP Right Cessation
- 1979-07-26 CA CA332,626A patent/CA1132560A/en not_active Expired
- 1979-07-27 DK DK318379A patent/DK318379A/da not_active Application Discontinuation
- 1979-07-28 JP JP9559979A patent/JPS5520785A/ja active Granted
-
1981
- 1981-05-11 US US06/262,145 patent/US4391980A/en not_active Expired - Lifetime
-
1987
- 1987-11-18 JP JP62289661A patent/JPS63253078A/ja active Granted
-
1988
- 1988-05-02 DK DK237588A patent/DK237588D0/da unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5319141A (en) * | 1989-09-25 | 1994-06-07 | Acic (Canada) Inc. | Process of making nadolol |
Also Published As
| Publication number | Publication date |
|---|---|
| US4294966A (en) | 1981-10-13 |
| DK237588A (da) | 1988-05-02 |
| JPH0152391B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1989-11-08 |
| JPS63253078A (ja) | 1988-10-20 |
| AU529335B2 (en) | 1983-06-02 |
| EP0007605B1 (de) | 1982-09-15 |
| FI792337A7 (fi) | 1980-01-29 |
| US4391980A (en) | 1983-07-05 |
| DK318379A (da) | 1980-01-29 |
| DE2963675D1 (en) | 1982-11-04 |
| JPS5520785A (en) | 1980-02-14 |
| EP0007605A1 (de) | 1980-02-06 |
| AU4925879A (en) | 1980-01-31 |
| ATE1547T1 (de) | 1982-09-15 |
| DK237588D0 (da) | 1988-05-02 |
| FI69051C (fi) | 1985-12-10 |
| JPS6364408B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-12-12 |
| ES482806A1 (es) | 1980-04-16 |
| FI69051B (fi) | 1985-08-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |