JPS61165367A

JPS61165367A - ラクタム化合物の製造方法

ラクタム化合物の製造方法

Info

Publication number: JPS61165367A
Authority: JP; Japan
Prior art keywords: group; groups; acid; formula; substituted
Prior art date: 1975-02-20
Legal status : Granted

Application number

JP61018307A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0258266B2 (enrdf_load_stackoverflow

Inventor

ラバト，バーンズ　ウツドワード

ハンス，ビツケル

Current Assignee

Novartis AG

Original Assignee

Ciba Geigy AG

Priority date

1975-02-20

Filing date

1986-01-31

Publication date

1986-07-26

1986-01-31 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1986-07-26 Publication of JPS61165367A publication Critical patent/JPS61165367A/ja

1990-12-07 Publication of JPH0258266B2 publication Critical patent/JPH0258266B2/ja

Status Granted legal-status Critical Current

Links

-1 lactam compound Chemical class 0.000 title description 624
238000004519 manufacturing process Methods 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims description 156
125000002252 acyl group Chemical group 0.000 claims description 94
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 93
238000000034 method Methods 0.000 claims description 62
125000001931 aliphatic group Chemical group 0.000 claims description 59
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 55
125000004432 carbon atom Chemical group C* 0.000 claims description 28
230000008569 process Effects 0.000 claims description 16
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
125000006239 protecting group Chemical group 0.000 claims description 11
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 7
229910052799 carbon Inorganic materials 0.000 claims description 7
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
239000000126 substance Substances 0.000 claims description 6
125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 4
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 223
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 171
239000002253 acid Substances 0.000 description 108
150000003839 salts Chemical class 0.000 description 98
125000000217 alkyl group Chemical group 0.000 description 87
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 82
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 81
239000000243 solution Substances 0.000 description 77
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 73
125000002887 hydroxy group Chemical group [H]O* 0.000 description 73
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 72
239000000203 mixture Substances 0.000 description 70
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
125000003545 alkoxy group Chemical group 0.000 description 68
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 63
125000003277 amino group Chemical group 0.000 description 62
238000006243 chemical reaction Methods 0.000 description 61
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 58
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 57
229940073584 methylene chloride Drugs 0.000 description 57
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 56
125000005843 halogen group Chemical group 0.000 description 53
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 49
239000003795 chemical substances by application Substances 0.000 description 44
150000002148 esters Chemical class 0.000 description 44
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 39
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
238000000862 absorption spectrum Methods 0.000 description 38
239000002904 solvent Substances 0.000 description 37
125000003118 aryl group Chemical group 0.000 description 36
125000004453 alkoxycarbonyl group Chemical group 0.000 description 35
150000003254 radicals Chemical class 0.000 description 35
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
125000001424 substituent group Chemical group 0.000 description 33
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 32
150000007513 acids Chemical class 0.000 description 32
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 32
229910052757 nitrogen Inorganic materials 0.000 description 32
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 31
229910052801 chlorine Inorganic materials 0.000 description 31
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 30
150000008064 anhydrides Chemical group 0.000 description 29
238000002844 melting Methods 0.000 description 29
230000008018 melting Effects 0.000 description 29
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 26
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
239000002585 base Substances 0.000 description 25
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 25
239000007858 starting material Substances 0.000 description 25
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 23
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 23
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 22
239000000741 silica gel Substances 0.000 description 22
229910002027 silica gel Inorganic materials 0.000 description 22
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
125000004423 acyloxy group Chemical group 0.000 description 20
229910052783 alkali metal Inorganic materials 0.000 description 20
239000003638 chemical reducing agent Substances 0.000 description 20
229910001385 heavy metal Inorganic materials 0.000 description 20
230000002378 acidificating effect Effects 0.000 description 19
125000000524 functional group Chemical group 0.000 description 19
125000000623 heterocyclic group Chemical group 0.000 description 19
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 18
150000001732 carboxylic acid derivatives Chemical class 0.000 description 18
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 17
125000001309 chloro group Chemical group Cl* 0.000 description 17
239000012299 nitrogen atmosphere Substances 0.000 description 17
239000011541 reaction mixture Substances 0.000 description 17
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 16
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
235000019253 formic acid Nutrition 0.000 description 16
150000002430 hydrocarbons Chemical group 0.000 description 16
238000003756 stirring Methods 0.000 description 16
238000004809 thin layer chromatography Methods 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
125000004466 alkoxycarbonylamino group Chemical group 0.000 description 15
230000032050 esterification Effects 0.000 description 15
238000005886 esterification reaction Methods 0.000 description 15
150000004820 halides Chemical class 0.000 description 15
239000000047 product Substances 0.000 description 15
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 15
238000002329 infrared spectrum Methods 0.000 description 14
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 14
229910052938 sodium sulfate Inorganic materials 0.000 description 14
235000011152 sodium sulphate Nutrition 0.000 description 14
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
125000004442 acylamino group Chemical group 0.000 description 13
150000001335 aliphatic alkanes Chemical class 0.000 description 13
125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 13
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 13
239000011261 inert gas Substances 0.000 description 13
239000011877 solvent mixture Substances 0.000 description 13
125000005237 alkyleneamino group Chemical group 0.000 description 12
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 12
150000001735 carboxylic acids Chemical class 0.000 description 12
239000000460 chlorine Substances 0.000 description 12
150000001805 chlorine compounds Chemical class 0.000 description 12
229930195733 hydrocarbon Natural products 0.000 description 12
230000007062 hydrolysis Effects 0.000 description 12
238000006460 hydrolysis reaction Methods 0.000 description 12
125000002950 monocyclic group Chemical group 0.000 description 12
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 12
229910052717 sulfur Inorganic materials 0.000 description 12
150000003973 alkyl amines Chemical class 0.000 description 11
150000004945 aromatic hydrocarbons Chemical class 0.000 description 11
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 11
239000003054 catalyst Substances 0.000 description 11
229910052736 halogen Inorganic materials 0.000 description 11
235000017557 sodium bicarbonate Nutrition 0.000 description 11
229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
239000004215 Carbon black (E152) Substances 0.000 description 10
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 10
125000003342 alkenyl group Chemical group 0.000 description 10
125000003282 alkyl amino group Chemical group 0.000 description 10
125000005907 alkyl ester group Chemical group 0.000 description 10
125000004414 alkyl thio group Chemical group 0.000 description 10
125000000753 cycloalkyl group Chemical group 0.000 description 10
125000004433 nitrogen atom Chemical group N* 0.000 description 10
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 10
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
229910052725 zinc Inorganic materials 0.000 description 10
239000011701 zinc Substances 0.000 description 10
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 9
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
238000005917 acylation reaction Methods 0.000 description 9
125000005236 alkanoylamino group Chemical group 0.000 description 9
150000002170 ethers Chemical class 0.000 description 9
229910052731 fluorine Inorganic materials 0.000 description 9
239000000543 intermediate Substances 0.000 description 9
239000002609 medium Substances 0.000 description 9
239000012074 organic phase Substances 0.000 description 9
SXBDXXFTJVHSAF-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-3-en-8-one Chemical class S1C=CCN2C(=O)C[C@H]21 SXBDXXFTJVHSAF-ZCFIWIBFSA-N 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
125000005276 alkyl hydrazino group Chemical group 0.000 description 8
125000002947 alkylene group Chemical group 0.000 description 8
238000010438 heat treatment Methods 0.000 description 8
239000012442 inert solvent Substances 0.000 description 8
229910052751 metal Inorganic materials 0.000 description 8
239000002184 metal Substances 0.000 description 8
150000007522 mineralic acids Chemical class 0.000 description 8
229910052698 phosphorus Inorganic materials 0.000 description 8
239000000376 reactant Substances 0.000 description 8
229920006395 saturated elastomer Polymers 0.000 description 8
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 8
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
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 7
239000012359 Methanesulfonyl chloride Substances 0.000 description 7
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 7
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 7
230000010933 acylation Effects 0.000 description 7
125000002723 alicyclic group Chemical group 0.000 description 7
125000001118 alkylidene group Chemical group 0.000 description 7
150000001412 amines Chemical class 0.000 description 7
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 7
238000001816 cooling Methods 0.000 description 7
229910001873 dinitrogen Inorganic materials 0.000 description 7
239000011737 fluorine Substances 0.000 description 7
125000002541 furyl group Chemical group 0.000 description 7
229910052739 hydrogen Inorganic materials 0.000 description 7
229910052740 iodine Inorganic materials 0.000 description 7
CHISLUGWUYZBFF-UHFFFAOYSA-L mercury(2+) 4-methylbenzenesulfinate Chemical compound [Hg++].Cc1ccc(cc1)S([O-])=O.Cc1ccc(cc1)S([O-])=O CHISLUGWUYZBFF-UHFFFAOYSA-L 0.000 description 7
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 7
150000007530 organic bases Chemical class 0.000 description 7
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
125000001476 phosphono group Chemical class [H]OP(*)(=O)O[H] 0.000 description 7
239000011574 phosphorus Substances 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
239000011734 sodium Substances 0.000 description 7
229910052708 sodium Inorganic materials 0.000 description 7
239000011780 sodium chloride Substances 0.000 description 7
159000000000 sodium salts Chemical class 0.000 description 7
238000001228 spectrum Methods 0.000 description 7
150000003460 sulfonic acids Chemical class 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 6
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 6
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 6
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
150000004649 carbonic acid derivatives Chemical class 0.000 description 6
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
238000000354 decomposition reaction Methods 0.000 description 6
238000006266 etherification reaction Methods 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
239000001257 hydrogen Substances 0.000 description 6
125000004464 hydroxyphenyl group Chemical group 0.000 description 6
150000002576 ketones Chemical class 0.000 description 6
ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 6
235000005985 organic acids Nutrition 0.000 description 6
125000000962 organic group Chemical group 0.000 description 6
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
239000007800 oxidant agent Substances 0.000 description 6
239000011591 potassium Chemical class 0.000 description 6
229910052700 potassium Inorganic materials 0.000 description 6
239000002994 raw material Substances 0.000 description 6
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 6
235000015424 sodium Nutrition 0.000 description 6
235000011121 sodium hydroxide Nutrition 0.000 description 6
238000003797 solvolysis reaction Methods 0.000 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 description 6
LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 6
FZEVMBJWXHDLDB-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical class S1CC=CN2C(=O)C[C@H]21 FZEVMBJWXHDLDB-ZCFIWIBFSA-N 0.000 description 5
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 5
VWQXZTFSQIIRQU-UHFFFAOYSA-N Cl.OC(=O)C1COCCO1 Chemical compound Cl.OC(=O)C1COCCO1 VWQXZTFSQIIRQU-UHFFFAOYSA-N 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
150000001298 alcohols Chemical class 0.000 description 5
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 5
150000005215 alkyl ethers Chemical class 0.000 description 5
150000003863 ammonium salts Chemical class 0.000 description 5
125000002619 bicyclic group Chemical group 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
150000001721 carbon Chemical group 0.000 description 5
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 5
150000004292 cyclic ethers Chemical class 0.000 description 5
150000002084 enol ethers Chemical class 0.000 description 5
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 5
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 5
125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 5
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238000010525 oxidative degradation reaction Methods 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
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ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
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MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
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238000003786 synthesis reaction Methods 0.000 description 1
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BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
150000003513 tertiary aromatic amines Chemical class 0.000 description 1
238000012360 testing method Methods 0.000 description 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
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HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
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XOGGUFAVLNCTRS-UHFFFAOYSA-N tetrapotassium;iron(2+);hexacyanide Chemical compound [K+].[K+].[K+].[K+].[Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] XOGGUFAVLNCTRS-UHFFFAOYSA-N 0.000 description 1
150000003536 tetrazoles Chemical class 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 1
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HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
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IBOKZQNMFSHYNQ-UHFFFAOYSA-N tribromosilane Chemical compound Br[SiH](Br)Br IBOKZQNMFSHYNQ-UHFFFAOYSA-N 0.000 description 1
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
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OLBXOAKEHMWSOV-UHFFFAOYSA-N triethyltin;hydrate Chemical compound O.CC[Sn](CC)CC OLBXOAKEHMWSOV-UHFFFAOYSA-N 0.000 description 1
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238000006227 trimethylsilylation reaction Methods 0.000 description 1
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238000005866 tritylation reaction Methods 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1
238000009777 vacuum freeze-drying Methods 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
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