DE2637176A1 - Carbonylmethylderivate - Google Patents

Info

Publication number

DE2637176A1

DE2637176A1 DE19762637176 DE2637176A DE2637176A1 DE 2637176 A1 DE2637176 A1 DE 2637176A1 DE 19762637176 DE19762637176 DE 19762637176 DE 2637176 A DE2637176 A DE 2637176A DE 2637176 A1 DE2637176 A1 DE 2637176A1

Authority

DE

Germany

Prior art keywords

cephem

amino

group

carboxylic acid

formula

Prior art date

1975-08-22

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.)

Withdrawn

Links

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• -1 CARBONYL METHYL Chemical class 0.000 title claims description 490
• 150000001875 compounds Chemical class 0.000 claims description 115
• 150000003839 salts Chemical class 0.000 claims description 106
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 89
• 229910052739 hydrogen Inorganic materials 0.000 claims description 76
• 239000001257 hydrogen Substances 0.000 claims description 75
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 71
• 239000002253 acid Substances 0.000 claims description 68
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 67
• 238000000034 method Methods 0.000 claims description 65
• 239000000203 mixture Substances 0.000 claims description 63
• 125000000217 alkyl group Chemical group 0.000 claims description 56
• 125000003545 alkoxy group Chemical group 0.000 claims description 51
• 229910052757 nitrogen Inorganic materials 0.000 claims description 46
• 150000002431 hydrogen Chemical class 0.000 claims description 43
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 41
• 239000003795 chemical substances by application Substances 0.000 claims description 38
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
• 125000002252 acyl group Chemical group 0.000 claims description 34
• 125000003277 amino group Chemical group 0.000 claims description 34
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
• 238000006243 chemical reaction Methods 0.000 claims description 26
• 239000007858 starting material Substances 0.000 claims description 22
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
• 125000003282 alkyl amino group Chemical group 0.000 claims description 20
• 229910052736 halogen Inorganic materials 0.000 claims description 20
• 125000006239 protecting group Chemical group 0.000 claims description 20
• 150000002367 halogens Chemical class 0.000 claims description 19
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 17
• 125000004432 carbon atom Chemical group C* 0.000 claims description 17
• 229930195733 hydrocarbon Natural products 0.000 claims description 14
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
• 239000004215 Carbon black (E152) Substances 0.000 claims description 13
• 125000002541 furyl group Chemical group 0.000 claims description 13
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 13
• 125000001544 thienyl group Chemical group 0.000 claims description 13
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 12
• 125000005276 alkyl hydrazino group Chemical group 0.000 claims description 12
• 239000003638 chemical reducing agent Substances 0.000 claims description 12
• 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 claims description 11
• 229910052783 alkali metal Inorganic materials 0.000 claims description 10
• 125000000524 functional group Chemical group 0.000 claims description 10
• 125000000623 heterocyclic group Chemical group 0.000 claims description 10
• 150000001340 alkali metals Chemical class 0.000 claims description 9
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 9
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 9
• 125000000676 alkoxyimino group Chemical group 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
• 125000000033 alkoxyamino group Chemical group 0.000 claims description 7
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
• 238000002360 preparation method Methods 0.000 claims description 7
• 239000011734 sodium Substances 0.000 claims description 7
• 239000011593 sulfur Substances 0.000 claims description 7
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
• 125000006016 2-bromoethoxy group Chemical group 0.000 claims description 6
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 6
• 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 239000001301 oxygen Substances 0.000 claims description 6
• 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims description 6
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
• 229910052708 sodium Inorganic materials 0.000 claims description 6
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 6
• 125000004423 acyloxy group Chemical group 0.000 claims description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
• 150000001768 cations Chemical class 0.000 claims description 5
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
• 150000003949 imides Chemical class 0.000 claims description 5
• 239000012442 inert solvent Substances 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 229910052700 potassium Inorganic materials 0.000 claims description 5
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 5
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 5
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
• 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 4
• 238000003776 cleavage reaction Methods 0.000 claims description 4
• 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 claims description 4
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 4
• 125000005842 heteroatom Chemical group 0.000 claims description 4
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
• 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 claims description 4
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 4
• 230000007017 scission Effects 0.000 claims description 4
• IKWLIQXIPRUIDU-ZCFIWIBFSA-N (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CCS[C@@H]2CC(=O)N12 IKWLIQXIPRUIDU-ZCFIWIBFSA-N 0.000 claims description 3
• 125000006012 2-chloroethoxy group Chemical group 0.000 claims description 3
• MAESPNMYPGGRCZ-VXGBXAGGSA-N C1[C@@H]2N(C1=O)C(=C(CS2)NC(=O)[C@@H](C3=CC=CC=C3)N)C(=O)O Chemical compound C1[C@@H]2N(C1=O)C(=C(CS2)NC(=O)[C@@H](C3=CC=CC=C3)N)C(=O)O MAESPNMYPGGRCZ-VXGBXAGGSA-N 0.000 claims description 3
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 3
• 125000004442 acylamino group Chemical group 0.000 claims description 3
• ORFCHEWUAUXSJW-XMSQKQJNSA-N benzhydryl (6r,7r)-7-amino-3-(2-methoxy-2-oxoethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound S([C@H]1N2C([C@H]1N)=O)CC(CC(=O)OC)=C2C(=O)OC(C=1C=CC=CC=1)C1=CC=CC=C1 ORFCHEWUAUXSJW-XMSQKQJNSA-N 0.000 claims description 3
• 239000007795 chemical reaction product Substances 0.000 claims description 3
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
• 125000004185 ester group Chemical group 0.000 claims description 3
• 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 3
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 3
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
• 125000005496 phosphonium group Chemical group 0.000 claims description 3
• 230000004962 physiological condition Effects 0.000 claims description 3
• 239000011591 potassium Substances 0.000 claims description 3
• 230000002829 reductive effect Effects 0.000 claims description 3
• YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 2
• 238000006136 alcoholysis reaction Methods 0.000 claims description 2
• 208000015181 infectious disease Diseases 0.000 claims description 2
• 239000013067 intermediate product Substances 0.000 claims description 2
• TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical group CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 claims description 2
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
• XUQFFXFKQRUPMO-PBFPGSCMSA-N (6R,7R)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-8-oxo-3-(2-oxopropyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C(C(=O)C)C=1CS[C@H]2N(C=1C(=O)O)C([C@H]2NC([C@H](N)C1=CC=CC=C1)=O)=O XUQFFXFKQRUPMO-PBFPGSCMSA-N 0.000 claims 1
• GWSKOWKLZXJWFZ-RHSMWYFYSA-N (6r,7r)-3-(2-methoxy-2-oxoethyl)-8-oxo-7-[(2-phenoxyacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)CC(=O)OC)C(O)=O)C(=O)COC1=CC=CC=C1 GWSKOWKLZXJWFZ-RHSMWYFYSA-N 0.000 claims 1
• 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 1
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
• 238000005903 acid hydrolysis reaction Methods 0.000 claims 1
• 238000005904 alkaline hydrolysis reaction Methods 0.000 claims 1
• 125000005189 alkyl hydroxy group Chemical group 0.000 claims 1
• 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims 1
• 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims 1
• 229910052744 lithium Inorganic materials 0.000 claims 1
• 125000005030 pyridylthio group Chemical group N1=C(C=CC=C1)S* 0.000 claims 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 162
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 138
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 115
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 97
• 239000000243 solution Substances 0.000 description 68
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 67
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 59
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 53
• 239000000741 silica gel Substances 0.000 description 51
• 229910002027 silica gel Inorganic materials 0.000 description 51
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 49
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 43
• 229910001868 water Inorganic materials 0.000 description 43
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 42
• 238000002329 infrared spectrum Methods 0.000 description 38
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 36
• 238000002211 ultraviolet spectrum Methods 0.000 description 35
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 30
• RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 30
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 28
• 125000003118 aryl group Chemical group 0.000 description 25
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 24
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
• 125000001931 aliphatic group Chemical group 0.000 description 22
• 150000003254 radicals Chemical class 0.000 description 22
• 239000002585 base Substances 0.000 description 21
• 239000002904 solvent Substances 0.000 description 21
• 229960000583 acetic acid Drugs 0.000 description 20
• 150000002148 esters Chemical class 0.000 description 20
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
• 239000002244 precipitate Substances 0.000 description 18
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 18
• 229920006395 saturated elastomer Polymers 0.000 description 18
• 239000000047 product Substances 0.000 description 17
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
• 150000007513 acids Chemical class 0.000 description 15
• 238000002844 melting Methods 0.000 description 15
• 230000008018 melting Effects 0.000 description 15
• UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 15
• 229940086542 triethylamine Drugs 0.000 description 15
• 150000008064 anhydrides Chemical class 0.000 description 14
• 239000012043 crude product Substances 0.000 description 14
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 13
• 235000017557 sodium bicarbonate Nutrition 0.000 description 13
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 13
• 238000005917 acylation reaction Methods 0.000 description 12
• 150000001412 amines Chemical class 0.000 description 12
• 239000000460 chlorine Substances 0.000 description 12
• OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 12
• 150000004820 halides Chemical class 0.000 description 12
• 239000011541 reaction mixture Substances 0.000 description 12
• 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 11
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
• 229910052938 sodium sulfate Inorganic materials 0.000 description 11
• 235000011152 sodium sulphate Nutrition 0.000 description 11
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
• 230000010933 acylation Effects 0.000 description 10
• 229910052751 metal Inorganic materials 0.000 description 10
• 239000000843 powder Substances 0.000 description 10
• 239000011780 sodium chloride Substances 0.000 description 10
• 230000002378 acidificating effect Effects 0.000 description 9
• 238000004587 chromatography analysis Methods 0.000 description 9
• 239000002184 metal Substances 0.000 description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 8
• 229910052801 chlorine Inorganic materials 0.000 description 8
• 238000000354 decomposition reaction Methods 0.000 description 8
• 230000032050 esterification Effects 0.000 description 8
• 238000005886 esterification reaction Methods 0.000 description 8
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 8
• 230000003647 oxidation Effects 0.000 description 8
• 238000007254 oxidation reaction Methods 0.000 description 8
• 229910052698 phosphorus Inorganic materials 0.000 description 8
• 239000011574 phosphorus Substances 0.000 description 8
• FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 8
• 125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 description 8
• 125000001424 substituent group Chemical group 0.000 description 8
• 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 7
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
• 150000001735 carboxylic acids Chemical class 0.000 description 7
• 238000010828 elution Methods 0.000 description 7
• 235000019253 formic acid Nutrition 0.000 description 7
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
• 239000012074 organic phase Substances 0.000 description 7
• 238000006722 reduction reaction Methods 0.000 description 7
• 238000004809 thin layer chromatography Methods 0.000 description 7
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
• 150000003973 alkyl amines Chemical class 0.000 description 6
• 150000003863 ammonium salts Chemical class 0.000 description 6
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 6
• 239000003054 catalyst Substances 0.000 description 6
• 239000000706 filtrate Substances 0.000 description 6
• 150000008282 halocarbons Chemical class 0.000 description 6
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
• 229910021529 ammonia Inorganic materials 0.000 description 5
• 229910052799 carbon Inorganic materials 0.000 description 5
• 238000001816 cooling Methods 0.000 description 5
• 230000007062 hydrolysis Effects 0.000 description 5
• 238000006460 hydrolysis reaction Methods 0.000 description 5
• 239000000543 intermediate Substances 0.000 description 5
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
• 239000002609 medium Substances 0.000 description 5
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• 229910052623 talc Inorganic materials 0.000 description 1
• 125000006633 tert-butoxycarbonylamino group Chemical group 0.000 description 1
• LVUBESNUUMLEHL-NSHDSACASA-N tert-butyl (2s)-6-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate Chemical compound CC(C)(C)OC(=O)N[C@H](C(=O)OC(C)(C)C)CCCCN LVUBESNUUMLEHL-NSHDSACASA-N 0.000 description 1
• 125000005922 tert-pentoxy group Chemical group 0.000 description 1
• 150000003513 tertiary aromatic amines Chemical class 0.000 description 1
• 150000003536 tetrazoles Chemical class 0.000 description 1
• 125000000335 thiazolyl group Chemical group 0.000 description 1
• 125000003396 thiol group Chemical group [H]S* 0.000 description 1
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
• AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
• 235000010487 tragacanth Nutrition 0.000 description 1
• 239000000196 tragacanth Substances 0.000 description 1
• 229940116362 tragacanth Drugs 0.000 description 1
• 125000005039 triarylmethyl group Chemical group 0.000 description 1
• 125000001425 triazolyl group Chemical group 0.000 description 1
• IBOKZQNMFSHYNQ-UHFFFAOYSA-N tribromosilane Chemical compound Br[SiH](Br)Br IBOKZQNMFSHYNQ-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
• CPRPKIMXLHBUGA-UHFFFAOYSA-N triethyltin Chemical compound CC[Sn](CC)CC CPRPKIMXLHBUGA-UHFFFAOYSA-N 0.000 description 1
• UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
• RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 description 1
• 239000000052 vinegar Substances 0.000 description 1
• 235000021419 vinegar Nutrition 0.000 description 1
• 238000012800 visualization Methods 0.000 description 1
• 238000005406 washing Methods 0.000 description 1