NO840646L - Fremstilling av optisk-aktive alfa-substituerte karboksylestere- og syrer - Google Patents
Fremstilling av optisk-aktive alfa-substituerte karboksylestere- og syrerInfo
- Publication number
- NO840646L NO840646L NO840646A NO840646A NO840646L NO 840646 L NO840646 L NO 840646L NO 840646 A NO840646 A NO 840646A NO 840646 A NO840646 A NO 840646A NO 840646 L NO840646 L NO 840646L
- Authority
- NO
- Norway
- Prior art keywords
- histidine
- group
- ketene
- carbon atoms
- cyclo
- Prior art date
Links
- -1 CARBOXYL Chemical class 0.000 title claims description 38
- 239000002253 acid Substances 0.000 title claims description 30
- 150000007513 acids Chemical class 0.000 title description 9
- 238000002360 preparation method Methods 0.000 title description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 78
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 29
- 239000003054 catalyst Substances 0.000 claims description 29
- 150000002148 esters Chemical class 0.000 claims description 28
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims description 28
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 27
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 26
- 125000003342 alkenyl group Chemical group 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 150000001413 amino acids Chemical class 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 20
- 235000001014 amino acid Nutrition 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 229920001184 polypeptide Polymers 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- 239000007795 chemical reaction product Substances 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 150000004820 halides Chemical class 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 150000001298 alcohols Chemical class 0.000 claims description 9
- 230000007062 hydrolysis Effects 0.000 claims description 9
- 238000006460 hydrolysis reaction Methods 0.000 claims description 9
- LSZVSCXZSRXVOA-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-methylbut-1-en-1-one Chemical compound CC(C)C(=C=O)C1=CC=C(Cl)C=C1 LSZVSCXZSRXVOA-UHFFFAOYSA-N 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- JDHILDINMRGULE-LURJTMIESA-N N(pros)-methyl-L-histidine Chemical compound CN1C=NC=C1C[C@H](N)C(O)=O JDHILDINMRGULE-LURJTMIESA-N 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 125000006239 protecting group Chemical group 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 108010092114 histidylphenylalanine Proteins 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- LUTLAXLNPLZCOF-UHFFFAOYSA-N 1-Methylhistidine Natural products OC(=O)C(N)(C)CC1=NC=CN1 LUTLAXLNPLZCOF-UHFFFAOYSA-N 0.000 claims description 5
- BRMWTNUJHUMWMS-UHFFFAOYSA-N 3-Methylhistidine Natural products CN1C=NC(CC(N)C(O)=O)=C1 BRMWTNUJHUMWMS-UHFFFAOYSA-N 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- YIWFXZNIBQBFHR-LURJTMIESA-N Gly-His Chemical compound [NH3+]CC(=O)N[C@H](C([O-])=O)CC1=CN=CN1 YIWFXZNIBQBFHR-LURJTMIESA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 108010020688 glycylhistidine Proteins 0.000 claims description 5
- 125000000487 histidyl group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C([H])=N1 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 5
- 150000003512 tertiary amines Chemical class 0.000 claims description 5
- 108010016626 Dipeptides Proteins 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- FRJIAZKQGSCKPQ-FSPLSTOPSA-N His-Ala Chemical compound OC(=O)[C@H](C)NC(=O)[C@@H](N)CC1=CN=CN1 FRJIAZKQGSCKPQ-FSPLSTOPSA-N 0.000 claims description 3
- XMAUFHMAAVTODF-STQMWFEESA-N His-Phe Chemical compound C([C@H](N)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)C1=CN=CN1 XMAUFHMAAVTODF-STQMWFEESA-N 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- 108010040030 histidinoalanine Proteins 0.000 claims description 3
- ZTVUZCVPVXCVRV-KBPBESRZSA-N (2S)-2-[[(2S)-2-amino-4-phenylbutanoyl]amino]-3-(1H-imidazol-5-yl)propanoic acid Chemical compound N[C@@H](CCC1=CC=CC=C1)C(=O)N[C@@H](CC1=CNC=N1)C(=O)O ZTVUZCVPVXCVRV-KBPBESRZSA-N 0.000 claims description 2
- KQLFYKBWIXSKHJ-KGLIPLIRSA-N (2S)-2-[[(3R)-3-amino-3-phenylpropanoyl]amino]-3-(3-methylimidazol-4-yl)propanoic acid Chemical compound N[C@@H](C1=CC=CC=C1)CC(=O)N[C@@H](CC1=CN=CN1C)C(=O)O KQLFYKBWIXSKHJ-KGLIPLIRSA-N 0.000 claims description 2
- NMXSWQMJOZUQKY-LBPRGKRZSA-N (2s)-2-amino-3-(1-benzylimidazol-4-yl)propanoic acid Chemical compound C1=NC(C[C@H](N)C(O)=O)=CN1CC1=CC=CC=C1 NMXSWQMJOZUQKY-LBPRGKRZSA-N 0.000 claims description 2
- OAXCYOTUTFGTCJ-ZETCQYMHSA-N (2s)-2-amino-3-(1-ethylimidazol-4-yl)propanoic acid Chemical compound CCN1C=NC(C[C@H](N)C(O)=O)=C1 OAXCYOTUTFGTCJ-ZETCQYMHSA-N 0.000 claims description 2
- ROSMBSOKFVZTHV-QMMMGPOBSA-N (2s)-2-amino-3-(1-propylimidazol-4-yl)propanoic acid Chemical compound CCCN1C=NC(C[C@H](N)C(O)=O)=C1 ROSMBSOKFVZTHV-QMMMGPOBSA-N 0.000 claims description 2
- KOAWDFCVOHGUFB-ZETCQYMHSA-N (2s)-2-amino-3-(3-ethylimidazol-4-yl)propanoic acid Chemical compound CCN1C=NC=C1C[C@H](N)C(O)=O KOAWDFCVOHGUFB-ZETCQYMHSA-N 0.000 claims description 2
- QFPUWKRRYFHMLA-QMMMGPOBSA-N (2s)-2-amino-3-(3-propylimidazol-4-yl)propanoic acid Chemical compound CCCN1C=NC=C1C[C@H](N)C(O)=O QFPUWKRRYFHMLA-QMMMGPOBSA-N 0.000 claims description 2
- CCHCEIHZCRIRNS-UHFFFAOYSA-N 2-azaniumyl-3-(3-benzylimidazol-4-yl)propanoate Chemical compound OC(=O)C(N)CC1=CN=CN1CC1=CC=CC=C1 CCHCEIHZCRIRNS-UHFFFAOYSA-N 0.000 claims description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- XZWXFWBHYRFLEF-FSPLSTOPSA-N Ala-His Chemical compound C[C@H](N)C(=O)N[C@H](C(O)=O)CC1=CN=CN1 XZWXFWBHYRFLEF-FSPLSTOPSA-N 0.000 claims description 2
- 108010085443 Anserine Proteins 0.000 claims description 2
- SGCGMORCWLEJNZ-UWVGGRQHSA-N His-His Chemical compound C([C@H]([NH3+])C(=O)N[C@@H](CC=1NC=NC=1)C([O-])=O)C1=CN=CN1 SGCGMORCWLEJNZ-UWVGGRQHSA-N 0.000 claims description 2
- LNCFUHAPNTYMJB-IUCAKERBSA-N His-Pro Chemical compound C([C@H](N)C(=O)N1[C@@H](CCC1)C(O)=O)C1=CN=CN1 LNCFUHAPNTYMJB-IUCAKERBSA-N 0.000 claims description 2
- SLRNWACWRVGMKD-UHFFFAOYSA-N L-anserine Natural products CN1C=NC(CC(NC(=O)CCN)C(O)=O)=C1 SLRNWACWRVGMKD-UHFFFAOYSA-N 0.000 claims description 2
- XEXSSIBQYNKFBX-KBPBESRZSA-N Phe-Gly-His Chemical compound C([C@H](N)C(=O)NCC(=O)N[C@@H](CC=1N=CNC=1)C(O)=O)C1=CC=CC=C1 XEXSSIBQYNKFBX-KBPBESRZSA-N 0.000 claims description 2
- OHUXOEXBXPZKPT-STQMWFEESA-N Phe-His Chemical compound C([C@H](N)C(=O)N[C@@H](CC=1N=CNC=1)C(O)=O)C1=CC=CC=C1 OHUXOEXBXPZKPT-STQMWFEESA-N 0.000 claims description 2
- 241000210053 Potentilla elegans Species 0.000 claims description 2
- 125000003295 alanine group Chemical group N[C@@H](C)C(=O)* 0.000 claims description 2
- 108010070944 alanylhistidine Proteins 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- HRRYYCWYCMJNGA-ZETCQYMHSA-N alpha-methyl-L-histidine Chemical compound OC(=O)[C@](N)(C)CC1=CN=CN1 HRRYYCWYCMJNGA-ZETCQYMHSA-N 0.000 claims description 2
- MYYIAHXIVFADCU-QMMMGPOBSA-N anserine Chemical compound CN1C=NC=C1C[C@H](NC(=O)CC[NH3+])C([O-])=O MYYIAHXIVFADCU-QMMMGPOBSA-N 0.000 claims description 2
- XAWDMXNJDWMHCN-KLXURFKVSA-N ethyl (2s)-2-amino-3-(1h-imidazol-5-yl)propanoate;dihydrochloride Chemical compound Cl.Cl.CCOC(=O)[C@@H](N)CC1=CN=CN1 XAWDMXNJDWMHCN-KLXURFKVSA-N 0.000 claims description 2
- 108010028295 histidylhistidine Proteins 0.000 claims description 2
- 108010085325 histidylproline Proteins 0.000 claims description 2
- XWOBNBRUDDUEEY-UHFFFAOYSA-N leucyl-histidine Chemical compound CC(C)CC(N)C(=O)NC(C(O)=O)CC1=CN=CN1 XWOBNBRUDDUEEY-UHFFFAOYSA-N 0.000 claims description 2
- VEEIFXWJNCAVEQ-RGMNGODLSA-N methyl (2s)-2-amino-3-(1h-imidazol-5-yl)propanoate;hydrochloride Chemical compound Cl.COC(=O)[C@@H](N)CC1=CNC=N1 VEEIFXWJNCAVEQ-RGMNGODLSA-N 0.000 claims description 2
- FPMLCYUEXWDCDX-WFASDCNBSA-N methyl (2s)-3-(1h-imidazol-5-yl)-2-[[(2s)-2-(phenylmethoxycarbonylamino)propanoyl]amino]propanoate Chemical compound C([C@@H](C(=O)OC)NC(=O)[C@H](C)NC(=O)OCC=1C=CC=CC=1)C1=CNC=N1 FPMLCYUEXWDCDX-WFASDCNBSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- XRGGOHBVSVCEDQ-KBPBESRZSA-N (2S)-2-[[(2S)-2-amino-3-phenylpropanoyl]-methylamino]-3-(1H-imidazol-5-yl)propanoic acid Chemical compound C([C@H](N(C)C(=O)[C@@H](N)CC=1C=CC=CC=1)C(O)=O)C1=CNC=N1 XRGGOHBVSVCEDQ-KBPBESRZSA-N 0.000 claims 1
- AULROAPTZJZHBY-KGLIPLIRSA-N (2S)-2-[[(3R)-3-amino-3-phenylpropanoyl]amino]-3-(1-methylimidazol-4-yl)propanoic acid Chemical compound N[C@@H](C1=CC=CC=C1)CC(=O)N[C@@H](CC1=CN(C=N1)C)C(=O)O AULROAPTZJZHBY-KGLIPLIRSA-N 0.000 claims 1
- 125000005282 allenyl group Chemical group 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 125000005289 uranyl group Chemical group 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 235000019441 ethanol Nutrition 0.000 description 32
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 26
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 239000007787 solid Substances 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 19
- 239000000047 product Substances 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 235000014304 histidine Nutrition 0.000 description 17
- 229960002885 histidine Drugs 0.000 description 16
- 229940024606 amino acid Drugs 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 9
- 150000002561 ketenes Chemical class 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 235000004279 alanine Nutrition 0.000 description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 6
- VTJMSIIXXKNIDJ-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-methylbutyric acid Chemical compound CC(C)C(C(O)=O)C1=CC=C(Cl)C=C1 VTJMSIIXXKNIDJ-UHFFFAOYSA-N 0.000 description 5
- HMARDGYLPHOTBP-UHFFFAOYSA-N 2-[4-(difluoromethoxy)phenyl]-3-methylbut-1-en-1-one Chemical compound CC(C)C(=C=O)C1=CC=C(OC(F)F)C=C1 HMARDGYLPHOTBP-UHFFFAOYSA-N 0.000 description 5
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 5
- 125000004414 alkyl thio group Chemical group 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
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- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
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- 238000001914 filtration Methods 0.000 description 4
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- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 description 3
- BWPYAVCZZUTOBY-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-methylbutanoyl chloride Chemical compound CC(C)C(C(Cl)=O)C1=CC=C(Cl)C=C1 BWPYAVCZZUTOBY-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000287828 Gallus gallus Species 0.000 description 3
- BRMWTNUJHUMWMS-LURJTMIESA-N N(tele)-methyl-L-histidine Chemical compound CN1C=NC(C[C@H](N)C(O)=O)=C1 BRMWTNUJHUMWMS-LURJTMIESA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- XPNGNIFUDRPBFJ-UHFFFAOYSA-N alpha-methylbenzylalcohol Natural products CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 125000002837 carbocyclic group Chemical group 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 150000007524 organic acids Chemical group 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
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- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
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- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
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- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- COLNVLDHVKWLRT-MRVPVSSYSA-N D-phenylalanine Chemical compound OC(=O)[C@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-MRVPVSSYSA-N 0.000 description 1
- 229930182832 D-phenylalanine Natural products 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 1
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 206010061307 Neck deformity Diseases 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-N 0.000 description 1
- BNQVUHQWZGTIBX-IUCAKERBSA-N Val-His Chemical compound CC(C)[C@H]([NH3+])C(=O)N[C@H](C([O-])=O)CC1=CN=CN1 BNQVUHQWZGTIBX-IUCAKERBSA-N 0.000 description 1
- KFYOBEKIRQPEQT-UHFFFAOYSA-N [4-[3-chloro-2-(trifluoromethyl)phenyl]phenyl]methyl n-(1-chloro-3-methyl-1-oxobutan-2-yl)carbamate Chemical compound C1=CC(COC(=O)NC(C(C)C)C(Cl)=O)=CC=C1C1=CC=CC(Cl)=C1C(F)(F)F KFYOBEKIRQPEQT-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001294 alanine derivatives Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
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- 125000003368 amide group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
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- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- VSSAZBXXNIABDN-UHFFFAOYSA-N cyclohexylmethanol Chemical compound OCC1CCCCC1 VSSAZBXXNIABDN-UHFFFAOYSA-N 0.000 description 1
- ZWJPCOALBPMBIC-UHFFFAOYSA-N diphenylketene Chemical compound C=1C=CC=CC=1C(=C=O)C1=CC=CC=C1 ZWJPCOALBPMBIC-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 150000002390 heteroarenes Chemical class 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 150000002410 histidine derivatives Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- AAAHCXVACIMZHZ-NHCUHLMSSA-N methyl (2r)-3-(1h-imidazol-5-yl)-2-[[(2r)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoyl]amino]propanoate Chemical compound C([C@H](C(=O)OC)NC(=O)[C@@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)C1=CN=CN1 AAAHCXVACIMZHZ-NHCUHLMSSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 125000005359 phenoxyalkyl group Chemical group 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/87—Preparation of ketenes or dimeric ketenes
- C07C45/89—Preparation of ketenes or dimeric ketenes from carboxylic acids, their anhydrides, esters or halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/88—Ketenes; Dimeric ketenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/46—Preparation of carboxylic acid esters from ketenes or polyketenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/12—Cyclic peptides with only normal peptide bonds in the ring
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46810083A | 1983-02-22 | 1983-02-22 | |
| US06/567,991 US4529810A (en) | 1983-02-22 | 1984-01-06 | Preparation of optically-active alpha-substituted carboxylic esters and acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO840646L true NO840646L (no) | 1984-08-23 |
Family
ID=27042282
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO840646A NO840646L (no) | 1983-02-22 | 1984-02-21 | Fremstilling av optisk-aktive alfa-substituerte karboksylestere- og syrer |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4529810A (da) |
| EP (1) | EP0116914A1 (da) |
| AU (1) | AU2426884A (da) |
| BR (1) | BR8400793A (da) |
| DD (1) | DD222006A5 (da) |
| DK (1) | DK83584A (da) |
| FI (1) | FI840681A (da) |
| GR (1) | GR79814B (da) |
| IL (1) | IL70887A0 (da) |
| NO (1) | NO840646L (da) |
| PL (1) | PL246322A1 (da) |
| PT (1) | PT78135B (da) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU576322B2 (en) * | 1983-07-22 | 1988-08-25 | Ici Australia Limited | Alpha-substituted-alpha-cyanomethyl alcohols |
| US4652670A (en) * | 1985-08-23 | 1987-03-24 | International Flavors & Fragrances Inc. | Cycloalkyl esters of mercaptoalkanoic acids |
| US4940813A (en) * | 1989-03-31 | 1990-07-10 | Merck & Co., Inc. | Resolution of a carboxylic acid |
| US5557518A (en) | 1994-04-28 | 1996-09-17 | Citibank, N.A. | Trusted agents for open electronic commerce |
| ES2141354T3 (es) * | 1994-06-13 | 2000-03-16 | Mitsubishi Rayon Co | Procedimiento para la obtencion de derivados de acidos carboxilicos, opticamente activos, con substitucion alfa. |
| DE19815833A1 (de) * | 1998-04-09 | 1999-10-14 | Basf Ag | Verfahren zur Herstellung von Linalylacetat |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3116474A1 (de) * | 1981-04-25 | 1982-11-11 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von optisch aktiven carbonsaeuren |
-
1984
- 1984-01-06 US US06/567,991 patent/US4529810A/en not_active Expired - Fee Related
- 1984-02-02 GR GR73697A patent/GR79814B/el unknown
- 1984-02-07 IL IL70887A patent/IL70887A0/xx unknown
- 1984-02-08 AU AU24268/84A patent/AU2426884A/en not_active Abandoned
- 1984-02-10 EP EP84101357A patent/EP0116914A1/en not_active Ceased
- 1984-02-20 FI FI840681A patent/FI840681A/fi not_active Application Discontinuation
- 1984-02-21 BR BR8400793A patent/BR8400793A/pt unknown
- 1984-02-21 NO NO840646A patent/NO840646L/no unknown
- 1984-02-21 DK DK83584A patent/DK83584A/da not_active Application Discontinuation
- 1984-02-21 PT PT78135A patent/PT78135B/pt unknown
- 1984-02-22 DD DD84260252A patent/DD222006A5/de unknown
- 1984-02-22 PL PL24632284A patent/PL246322A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI840681A (fi) | 1984-08-23 |
| PT78135A (en) | 1984-03-01 |
| DD222006A5 (de) | 1985-05-08 |
| AU2426884A (en) | 1984-08-30 |
| PL246322A1 (en) | 1985-09-10 |
| DK83584A (da) | 1984-08-23 |
| EP0116914A1 (en) | 1984-08-29 |
| IL70887A0 (en) | 1984-05-31 |
| FI840681A0 (fi) | 1984-02-20 |
| BR8400793A (pt) | 1984-09-25 |
| US4529810A (en) | 1985-07-16 |
| DK83584D0 (da) | 1984-02-21 |
| GR79814B (da) | 1984-10-31 |
| PT78135B (en) | 1986-05-19 |
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