BE848545A

BE848545A - Derives n-methylene substitues de thienamycine,

Derives n-methylene substitues de thienamycine,

Info

Publication number: BE848545A
Authority: BE; Belgium
Prior art keywords: emi; carbon atoms; alkyl; compound according; hydrogen
Prior art date: 1975-11-21

Application number

BE172525A

Other languages

English (en)

French (fr)

Priority date

1975-11-21

Filing date

1976-11-19

Publication date

1977-05-20

1976-11-19 Application filed filed Critical

1977-05-20 Publication of BE848545A publication Critical patent/BE848545A/fr

Links

-1 nitro, hydroxyl Chemical group 0.000 claims description 264
125000004432 carbon atom Chemical group C* 0.000 claims description 123
125000000217 alkyl group Chemical group 0.000 claims description 81
150000001875 compounds Chemical class 0.000 claims description 68
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 58
238000002360 preparation method Methods 0.000 claims description 47
229910052757 nitrogen Inorganic materials 0.000 claims description 43
239000001257 hydrogen Substances 0.000 claims description 29
229910052739 hydrogen Inorganic materials 0.000 claims description 29
238000000034 method Methods 0.000 claims description 28
125000003118 aryl group Chemical group 0.000 claims description 23
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
125000003342 alkenyl group Chemical group 0.000 claims description 21
229910052717 sulfur Inorganic materials 0.000 claims description 21
150000002148 esters Chemical class 0.000 claims description 20
150000003254 radicals Chemical class 0.000 claims description 20
125000001424 substituent group Chemical group 0.000 claims description 20
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 19
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 19
239000011593 sulfur Substances 0.000 claims description 19
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
125000003545 alkoxy group Chemical group 0.000 claims description 18
125000002252 acyl group Chemical group 0.000 claims description 17
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
229910052760 oxygen Inorganic materials 0.000 claims description 17
239000001301 oxygen Substances 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
125000003710 aryl alkyl group Chemical group 0.000 claims description 14
125000004429 atom Chemical group 0.000 claims description 13
125000005842 heteroatom Chemical group 0.000 claims description 12
238000004519 manufacturing process Methods 0.000 claims description 12
150000004820 halides Chemical class 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 10
125000000623 heterocyclic group Chemical group 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 9
150000001408 amides Chemical class 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
125000002950 monocyclic group Chemical group 0.000 claims description 8
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 7
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
239000002168 alkylating agent Substances 0.000 claims description 7
229940100198 alkylating agent Drugs 0.000 claims description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
229910052794 bromium Inorganic materials 0.000 claims description 7
239000002552 dosage form Substances 0.000 claims description 7
150000002170 ethers Chemical class 0.000 claims description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
230000000694 effects Effects 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
125000004475 heteroaralkyl group Chemical group 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 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
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
239000000463 material Substances 0.000 claims description 5
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 4
125000000304 alkynyl group Chemical group 0.000 claims description 4
125000004103 aminoalkyl group Chemical group 0.000 claims description 4
125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 4
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
125000004122 cyclic group Chemical group 0.000 claims description 4
125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
239000011737 fluorine Substances 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
125000004423 acyloxy group Chemical group 0.000 claims description 3
125000005041 acyloxyalkyl group Chemical group 0.000 claims description 3
229910052784 alkaline earth metal Chemical group 0.000 claims description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
125000001072 heteroaryl group Chemical group 0.000 claims description 3
125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 3
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 3
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
229910052698 phosphorus Inorganic materials 0.000 claims description 3
239000011574 phosphorus Substances 0.000 claims description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
108090000623 proteins and genes Proteins 0.000 claims description 3
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
125000004954 trialkylamino group Chemical group 0.000 claims description 3
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims description 2
125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 2
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000001721 carboxyacetyl group Chemical group 0.000 claims description 2
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims description 2
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
125000000350 glycoloyl group Chemical group O=C([*])C([H])([H])O[H] 0.000 claims description 2
125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 2
125000005633 phthalidyl group Chemical group 0.000 claims description 2
125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
125000006413 ring segment Chemical group 0.000 claims description 2
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 2
125000000129 anionic group Chemical group 0.000 claims 2
239000003937 drug carrier Substances 0.000 claims 2
125000006022 2-methyl-2-propenyl group Chemical group 0.000 claims 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
239000003513 alkali Chemical group 0.000 claims 1
125000004663 dialkyl amino group Chemical group 0.000 claims 1
125000006351 ethylthiomethyl group Chemical group [H]C([H])([H])C([H])([H])SC([H])([H])* 0.000 claims 1
125000004404 heteroalkyl group Chemical group 0.000 claims 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
239000011630 iodine Substances 0.000 claims 1
238000012986 modification Methods 0.000 claims 1
230000004048 modification Effects 0.000 claims 1
230000035943 smell Effects 0.000 claims 1
239000000243 solution Substances 0.000 description 91
239000000203 mixture Substances 0.000 description 78
WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 description 74
WKDDRNSBRWANNC-ATRFCDNQSA-N Thienamycin Chemical compound C1C(SCCN)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 WKDDRNSBRWANNC-ATRFCDNQSA-N 0.000 description 73
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 57
238000006243 chemical reaction Methods 0.000 description 53
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 51
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
239000000047 product Substances 0.000 description 32
229910001868 water Inorganic materials 0.000 description 28
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 27
239000002904 solvent Substances 0.000 description 25
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
239000007787 solid Substances 0.000 description 23
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
239000008367 deionised water Substances 0.000 description 21
229910021641 deionized water Inorganic materials 0.000 description 21
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
230000003115 biocidal effect Effects 0.000 description 20
239000003153 chemical reaction reagent Substances 0.000 description 20
239000007858 starting material Substances 0.000 description 20
239000008363 phosphate buffer Substances 0.000 description 19
239000011541 reaction mixture Substances 0.000 description 17
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 16
239000003242 anti bacterial agent Substances 0.000 description 16
229940088710 antibiotic agent Drugs 0.000 description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
239000002253 acid Substances 0.000 description 13
230000000903 blocking effect Effects 0.000 description 13
239000010410 layer Substances 0.000 description 13
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
239000004480 active ingredient Substances 0.000 description 11
239000000872 buffer Substances 0.000 description 11
239000007788 liquid Substances 0.000 description 11
239000000741 silica gel Substances 0.000 description 11
229910002027 silica gel Inorganic materials 0.000 description 11
125000003277 amino group Chemical group 0.000 description 10
229910052943 magnesium sulfate Inorganic materials 0.000 description 10
235000019341 magnesium sulphate Nutrition 0.000 description 10
239000000725 suspension Substances 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000000706 filtrate Substances 0.000 description 9
239000002245 particle Substances 0.000 description 9
239000011347 resin Substances 0.000 description 9
229920005989 resin Polymers 0.000 description 9
239000000523 sample Substances 0.000 description 9
239000012267 brine Substances 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
238000004587 chromatography analysis Methods 0.000 description 8
235000008504 concentrate Nutrition 0.000 description 8
239000012141 concentrate Substances 0.000 description 8
238000010586 diagram Methods 0.000 description 8
238000001704 evaporation Methods 0.000 description 8
230000008020 evaporation Effects 0.000 description 8
239000003921 oil Substances 0.000 description 8
235000019198 oils Nutrition 0.000 description 8
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
238000003756 stirring Methods 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
229910052783 alkali metal Inorganic materials 0.000 description 7
150000001409 amidines Chemical class 0.000 description 7
239000002585 base Substances 0.000 description 7
238000005984 hydrogenation reaction Methods 0.000 description 7
150000002463 imidates Chemical class 0.000 description 7
238000012360 testing method Methods 0.000 description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
238000000855 fermentation Methods 0.000 description 6
230000004151 fermentation Effects 0.000 description 6
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 6
230000007062 hydrolysis Effects 0.000 description 6
238000006460 hydrolysis reaction Methods 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 6
239000002808 molecular sieve Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 6
239000011780 sodium chloride Substances 0.000 description 6
YFLNKMDUUCRCSU-UHFFFAOYSA-N 4-(2-hydroxyethyl)azetidin-2-one Chemical compound OCCC1CC(=O)N1 YFLNKMDUUCRCSU-UHFFFAOYSA-N 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
150000001340 alkali metals Chemical class 0.000 description 5
150000008064 anhydrides Chemical class 0.000 description 5
239000008346 aqueous phase Substances 0.000 description 5
125000002619 bicyclic group Chemical group 0.000 description 5
238000000605 extraction Methods 0.000 description 5
238000004128 high performance liquid chromatography Methods 0.000 description 5
230000014759 maintenance of location Effects 0.000 description 5
239000012071 phase Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
239000006228 supernatant Substances 0.000 description 5
239000003826 tablet Substances 0.000 description 5
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 5
WGMHMVLZFAJNOT-UHFFFAOYSA-N 1-ethoxyethylideneazanium;chloride Chemical compound [Cl-].CCOC(C)=[NH2+] WGMHMVLZFAJNOT-UHFFFAOYSA-N 0.000 description 4
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 4
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
241000894006 Bacteria Species 0.000 description 4
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
125000003047 N-acetyl group Chemical group 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
150000008065 acid anhydrides Chemical class 0.000 description 4
238000005917 acylation reaction Methods 0.000 description 4
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000012043 crude product Substances 0.000 description 4
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 4
238000001962 electrophoresis Methods 0.000 description 4
238000010828 elution Methods 0.000 description 4
239000000499 gel Substances 0.000 description 4
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 4
239000005457 ice water Substances 0.000 description 4
150000002464 imidothioesters Chemical class 0.000 description 4
239000008101 lactose Substances 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
239000003495 polar organic solvent Substances 0.000 description 4
238000012545 processing Methods 0.000 description 4
238000010992 reflux Methods 0.000 description 4
241000894007 species Species 0.000 description 4
230000008511 vegetative development Effects 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
229920001817 Agar Polymers 0.000 description 3
108010010803 Gelatin Proteins 0.000 description 3
229930182555 Penicillin Natural products 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
241000191967 Staphylococcus aureus Species 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001266 acyl halides Chemical class 0.000 description 3
239000008272 agar Substances 0.000 description 3
230000001476 alcoholic effect Effects 0.000 description 3
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 3
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