GB1588111A

GB1588111A - Esters and thiolesters of amino acids intermediates therefor processes for their production and compositions including them

Esters and thiolesters of amino acids intermediates therefor processes for their production and compositions including them Download PDF

Info

Publication number: GB1588111A
Authority: GB; United Kingdom
Prior art keywords: valine; ester; fluoro; phenoxybenzyl; hydrogen
Prior art date: 1977-03-21
Legal status : Expired

Application number

GB9026/78A

Other languages

English (en)

Current Assignee

Zoecon Corp

Original Assignee

Zoecon Corp

Priority date

1977-03-21

Filing date

1978-03-07

Publication date

1981-04-15

1978-02-16 Priority claimed from US05/878,091 external-priority patent/US4243819A/en

1978-03-07 Application filed by Zoecon Corp filed Critical Zoecon Corp

1981-04-15 Publication of GB1588111A publication Critical patent/GB1588111A/en

Status Expired legal-status Critical Current

Links

150000002148 esters Chemical class 0.000 title claims abstract description 53
238000000034 method Methods 0.000 title claims description 98
239000000203 mixture Substances 0.000 title claims description 55
238000004519 manufacturing process Methods 0.000 title claims description 3
150000001413 amino acids Chemical class 0.000 title abstract description 10
150000007970 thio esters Chemical class 0.000 title abstract description 10
239000000543 intermediate Substances 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 67
-1 m - phenoxybenzyl ester Chemical class 0.000 claims description 253
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 80
FBCHRMFAWNWJCU-JTQLQIEISA-N (2s)-2-(4-chloroanilino)-3-methylbutanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC1=CC=C(Cl)C=C1 FBCHRMFAWNWJCU-JTQLQIEISA-N 0.000 claims description 55
239000001257 hydrogen Substances 0.000 claims description 43
229910052739 hydrogen Inorganic materials 0.000 claims description 43
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 37
DLULJAUWRRKBML-JTQLQIEISA-N (2s)-2-[2-fluoro-4-(trifluoromethyl)anilino]-3-methylbutanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC1=CC=C(C(F)(F)F)C=C1F DLULJAUWRRKBML-JTQLQIEISA-N 0.000 claims description 35
125000004432 carbon atom Chemical group C* 0.000 claims description 35
125000000217 alkyl group Chemical group 0.000 claims description 30
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
150000002431 hydrogen Chemical class 0.000 claims description 25
239000002253 acid Substances 0.000 claims description 22
KZPLXTSZVZBJPO-JTQLQIEISA-N (2s)-2-(4-chloro-2-fluoroanilino)-3-methylbutanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC1=CC=C(Cl)C=C1F KZPLXTSZVZBJPO-JTQLQIEISA-N 0.000 claims description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
NZPWGWAEKDSVFN-JTQLQIEISA-N (2s)-3-methyl-2-[4-(trifluoromethyl)anilino]butanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC1=CC=C(C(F)(F)F)C=C1 NZPWGWAEKDSVFN-JTQLQIEISA-N 0.000 claims description 15
125000001153 fluoro group Chemical group F* 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 14
YKSHSSFDOHACTC-JTQLQIEISA-N (2s)-2-[2-chloro-4-(trifluoromethyl)anilino]-3-methylbutanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC1=CC=C(C(F)(F)F)C=C1Cl YKSHSSFDOHACTC-JTQLQIEISA-N 0.000 claims description 13
241000238631 Hexapoda Species 0.000 claims description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
241000607479 Yersinia pestis Species 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 12
125000003342 alkenyl group Chemical group 0.000 claims description 11
125000003710 aryl alkyl group Chemical group 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 11
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
CAXWIGJTXJTLLU-JTQLQIEISA-N (2s)-2-(4-bromo-2-fluoroanilino)-3-methylbutanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC1=CC=C(Br)C=C1F CAXWIGJTXJTLLU-JTQLQIEISA-N 0.000 claims description 10
LYJVJCQYQYSJHU-NSHDSACASA-N (2s)-2-(2-fluoro-4-methylanilino)-3-methylbutanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC1=CC=C(C)C=C1F LYJVJCQYQYSJHU-NSHDSACASA-N 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 9
125000000304 alkynyl group Chemical group 0.000 claims description 9
125000004414 alkyl thio group Chemical group 0.000 claims description 8
125000001309 chloro group Chemical group Cl* 0.000 claims description 8
125000001188 haloalkyl group Chemical group 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 8
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 7
MEFVUVHUSRMQFS-NSHDSACASA-N (2s)-2-(3-fluoro-4-methylanilino)-3-methylbutanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC1=CC=C(C)C(F)=C1 MEFVUVHUSRMQFS-NSHDSACASA-N 0.000 claims description 6
241000238876 Acari Species 0.000 claims description 6
125000003302 alkenyloxy group Chemical group 0.000 claims description 6
125000001246 bromo group Chemical group Br* 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
125000000262 haloalkenyl group Chemical group 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
239000007787 solid Substances 0.000 claims description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
125000004423 acyloxy group Chemical group 0.000 claims description 5
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 5
239000012141 concentrate Substances 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
125000004438 haloalkoxy group Chemical group 0.000 claims description 5
150000007522 mineralic acids Chemical class 0.000 claims description 5
150000007524 organic acids Chemical class 0.000 claims description 5
241001124076 Aphididae Species 0.000 claims description 4
241000255925 Diptera Species 0.000 claims description 4
241000238887 Ornithodoros Species 0.000 claims description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
125000005133 alkynyloxy group Chemical group 0.000 claims description 4
125000005129 aryl carbonyl group Chemical group 0.000 claims description 4
125000005110 aryl thio group Chemical group 0.000 claims description 4
125000004104 aryloxy group Chemical group 0.000 claims description 4
125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
125000003963 dichloro group Chemical group Cl* 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 claims description 3
241001425390 Aphis fabae Species 0.000 claims description 3
241000819999 Nymphes Species 0.000 claims description 3
241001454293 Tetranychus urticae Species 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000005291 haloalkenyloxy group Chemical group 0.000 claims description 3
125000004995 haloalkylthio group Chemical group 0.000 claims description 3
125000000232 haloalkynyl group Chemical group 0.000 claims description 3
239000007788 liquid Substances 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
235000005985 organic acids Nutrition 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 claims description 2
241000254173 Coleoptera Species 0.000 claims description 2
241000256244 Heliothis virescens Species 0.000 claims description 2
241000258937 Hemiptera Species 0.000 claims description 2
241001466007 Heteroptera Species 0.000 claims description 2
241000257303 Hymenoptera Species 0.000 claims description 2
241000255777 Lepidoptera Species 0.000 claims description 2
241000238814 Orthoptera Species 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
241001454295 Tetranychidae Species 0.000 claims description 2
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 2
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 2
229940098779 methanesulfonic acid Drugs 0.000 claims description 2
229910052717 sulfur Chemical group 0.000 claims description 2
239000011593 sulfur Chemical group 0.000 claims description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims 2
230000000895 acaricidal effect Effects 0.000 abstract 1
230000000749 insecticidal effect Effects 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 226
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 73
238000006243 chemical reaction Methods 0.000 description 68
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 54
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 50
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 44
UJUNUASMYSTBSK-UHFFFAOYSA-N 1-(bromomethyl)-3-phenoxybenzene Chemical compound BrCC1=CC=CC(OC=2C=CC=CC=2)=C1 UJUNUASMYSTBSK-UHFFFAOYSA-N 0.000 description 41
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 41
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
239000012267 brine Substances 0.000 description 38
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 36
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
235000019441 ethanol Nutrition 0.000 description 34
239000011541 reaction mixture Substances 0.000 description 33
239000000243 solution Substances 0.000 description 33
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
AJWAECPVBMQFSX-NSHDSACASA-N (2s)-3-methyl-2-(4-methylanilino)butanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC1=CC=C(C)C=C1 AJWAECPVBMQFSX-NSHDSACASA-N 0.000 description 25
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 25
229910000027 potassium carbonate Inorganic materials 0.000 description 25
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 24
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 22
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 21
239000004474 valine Substances 0.000 description 21
239000002904 solvent Substances 0.000 description 20
KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 18
229910052757 nitrogen Inorganic materials 0.000 description 18
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 17
229910052938 sodium sulfate Inorganic materials 0.000 description 17
235000011152 sodium sulphate Nutrition 0.000 description 17
238000004809 thin layer chromatography Methods 0.000 description 17
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
239000012259 ether extract Substances 0.000 description 15
239000010410 layer Substances 0.000 description 15
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 14
159000000000 sodium salts Chemical class 0.000 description 14
238000003756 stirring Methods 0.000 description 14
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 13
239000005457 ice water Substances 0.000 description 13
239000008346 aqueous phase Substances 0.000 description 12
RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 9
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 9
239000012071 phase Substances 0.000 description 9
238000012746 preparative thin layer chromatography Methods 0.000 description 9
239000000047 product Substances 0.000 description 9
MBRPCSKHPRLQQQ-JTQLQIEISA-N (2s)-2-anilino-3-methylbutanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC1=CC=CC=C1 MBRPCSKHPRLQQQ-JTQLQIEISA-N 0.000 description 8
UEBARDWJXBGYEJ-UHFFFAOYSA-N 2-bromo-3-methylbutanoic acid Chemical compound CC(C)C(Br)C(O)=O UEBARDWJXBGYEJ-UHFFFAOYSA-N 0.000 description 8
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 8
229940024606 amino acid Drugs 0.000 description 8
239000007795 chemical reaction product Substances 0.000 description 8
230000007935 neutral effect Effects 0.000 description 8
KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 8
238000010992 reflux Methods 0.000 description 8
UFFBMTHBGFGIHF-UHFFFAOYSA-N (2,6-Me2C6H3)NH2 Natural products CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 7
238000001035 drying Methods 0.000 description 7
238000001704 evaporation Methods 0.000 description 7
238000001914 filtration Methods 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
235000017557 sodium bicarbonate Nutrition 0.000 description 7
229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 7
XCAMLAFYNOLVPM-NSHDSACASA-N (2s)-2-(2,6-dimethylanilino)-3-methylbutanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC1=C(C)C=CC=C1C XCAMLAFYNOLVPM-NSHDSACASA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
239000012043 crude product Substances 0.000 description 6
WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
238000005192 partition Methods 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
CQVOILYSLSWABZ-NSHDSACASA-N (2s)-2-(2-fluoro-4-methoxyanilino)-3-methylbutanoic acid Chemical compound COC1=CC=C(N[C@@H](C(C)C)C(O)=O)C(F)=C1 CQVOILYSLSWABZ-NSHDSACASA-N 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
CSFDTBRRIBJILD-UHFFFAOYSA-N 4-chloro-2-fluoroaniline Chemical compound NC1=CC=C(Cl)C=C1F CSFDTBRRIBJILD-UHFFFAOYSA-N 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
230000003197 catalytic effect Effects 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
XWTQCMHYIJEQPD-JTQLQIEISA-N (2s)-2-(4-chloro-3-fluoroanilino)-3-methylbutanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC1=CC=C(Cl)C(F)=C1 XWTQCMHYIJEQPD-JTQLQIEISA-N 0.000 description 4
XZUCJVTXERYPQH-NSHDSACASA-N (2s)-2-(4-methoxyanilino)-3-methylbutanoic acid Chemical compound COC1=CC=C(N[C@@H](C(C)C)C(O)=O)C=C1 XZUCJVTXERYPQH-NSHDSACASA-N 0.000 description 4
MFOQAAROVBJMNI-ZDUSSCGKSA-N (2s)-2-(4-tert-butylanilino)-3-methylbutanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC1=CC=C(C(C)(C)C)C=C1 MFOQAAROVBJMNI-ZDUSSCGKSA-N 0.000 description 4
IUKZSVHIWMVLEQ-NSHDSACASA-N (2s)-3-methyl-2-(2-methylanilino)butanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC1=CC=CC=C1C IUKZSVHIWMVLEQ-NSHDSACASA-N 0.000 description 4
ZQEXBVHABAJPHJ-UHFFFAOYSA-N 2-fluoro-4-methylaniline Chemical compound CC1=CC=C(N)C(F)=C1 ZQEXBVHABAJPHJ-UHFFFAOYSA-N 0.000 description 4
RMXZAXNAIMJGCX-UHFFFAOYSA-N 3-[2-fluoro-4-(trifluoromethyl)phenyl]-4-propan-2-yl-1,3-oxazolidine-2,5-dione Chemical compound O=C1OC(=O)C(C(C)C)N1C1=CC=C(C(F)(F)F)C=C1F RMXZAXNAIMJGCX-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 4
239000007789 gas Substances 0.000 description 4
150000004820 halides Chemical class 0.000 description 4
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
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150000004702 methyl esters Chemical class 0.000 description 4
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