CH632510A5 - Process for preparing amidines - Google Patents

Info

Publication number

CH632510A5

CH632510A5 CH1462376A CH1462376A CH632510A5 CH 632510 A5 CH632510 A5 CH 632510A5 CH 1462376 A CH1462376 A CH 1462376A CH 1462376 A CH1462376 A CH 1462376A CH 632510 A5 CH632510 A5 CH 632510A5

Authority

CH

Switzerland

Prior art keywords

carbon atoms

group

alkyl

substituted

cooh

Prior art date

1975-11-21

Links

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• 150000001409 amidines Chemical class 0.000 title claims description 16
• 238000004519 manufacturing process Methods 0.000 title description 21
• -1 heteroaralkyl radical Chemical class 0.000 claims description 404
• 125000004432 carbon atom Chemical group C* 0.000 claims description 167
• 125000000217 alkyl group Chemical group 0.000 claims description 92
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 66
• 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 claims description 61
• WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 claims description 61
• 238000002360 preparation method Methods 0.000 claims description 48
• 229910052739 hydrogen Inorganic materials 0.000 claims description 47
• 229910052757 nitrogen Inorganic materials 0.000 claims description 46
• 238000000034 method Methods 0.000 claims description 45
• 239000001257 hydrogen Substances 0.000 claims description 42
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
• 229910052760 oxygen Inorganic materials 0.000 claims description 35
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 31
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 31
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 30
• 125000003545 alkoxy group Chemical group 0.000 claims description 29
• 229910052717 sulfur Inorganic materials 0.000 claims description 29
• 150000001875 compounds Chemical class 0.000 claims description 28
• 125000003118 aryl group Chemical group 0.000 claims description 27
• 239000001301 oxygen Substances 0.000 claims description 27
• 125000001424 substituent group Chemical group 0.000 claims description 27
• 239000000460 chlorine Substances 0.000 claims description 26
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
• 125000005842 heteroatom Chemical group 0.000 claims description 25
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
• 150000003839 salts Chemical class 0.000 claims description 23
• 239000011593 sulfur Substances 0.000 claims description 22
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 21
• 150000003254 radicals Chemical class 0.000 claims description 21
• 125000002252 acyl group Chemical group 0.000 claims description 20
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
• 125000003342 alkenyl group Chemical group 0.000 claims description 19
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
• 229910052801 chlorine Inorganic materials 0.000 claims description 17
• 150000002148 esters Chemical class 0.000 claims description 17
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 16
• 229910052736 halogen Inorganic materials 0.000 claims description 16
• 150000002367 halogens Chemical class 0.000 claims description 16
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 15
• 229910052731 fluorine Inorganic materials 0.000 claims description 14
• 125000002950 monocyclic group Chemical group 0.000 claims description 14
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 13
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
• 229910052794 bromium Inorganic materials 0.000 claims description 13
• 239000011737 fluorine Substances 0.000 claims description 13
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
• 125000004429 atom Chemical group 0.000 claims description 12
• 125000000623 heterocyclic group Chemical group 0.000 claims description 12
• 150000002431 hydrogen Chemical class 0.000 claims description 11
• 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 10
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
• 125000004475 heteroaralkyl group Chemical group 0.000 claims description 9
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
• 125000006413 ring segment Chemical group 0.000 claims description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
• 150000002463 imidates Chemical class 0.000 claims description 8
• 125000004423 acyloxy group Chemical group 0.000 claims description 7
• 125000004414 alkyl thio group Chemical group 0.000 claims description 7
• 125000000304 alkynyl group Chemical group 0.000 claims description 7
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 7
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
• 229910052740 iodine Inorganic materials 0.000 claims description 7
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 6
• 125000002619 bicyclic group Chemical group 0.000 claims description 6
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 6
• 125000000717 hydrazino group Chemical group [H]N([*])N([H])[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
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-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
• 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 5
• 125000005242 carbamoyl alkyl group Chemical group 0.000 claims description 5
• 229910052799 carbon Inorganic materials 0.000 claims description 5
• 125000004122 cyclic group Chemical group 0.000 claims description 5
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
• 125000001188 haloalkyl group Chemical group 0.000 claims description 5
• 125000001072 heteroaryl group Chemical group 0.000 claims description 5
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 5
• 239000011630 iodine Substances 0.000 claims description 5
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
• 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 description 4
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
• 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims description 4
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
• SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 claims description 3
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 3
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 3
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 3
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
• 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 3
• 125000003282 alkyl amino group Chemical group 0.000 claims description 3
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 3
• 125000004104 aryloxy group Chemical group 0.000 claims description 3
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 3
• 125000005356 cycloalkylalkenyl group Chemical group 0.000 claims description 3
• 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 3
• 125000001453 quaternary ammonium group Chemical group 0.000 claims description 3
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 3
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 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
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 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
• 125000005010 perfluoroalkyl group Chemical group 0.000 claims 2
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 1
• 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 1
• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 1
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
• 125000001309 chloro group Chemical group Cl* 0.000 claims 1
• 125000004985 dialkyl amino alkyl 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
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 118
• 239000000243 solution Substances 0.000 description 93
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 85
• 239000000203 mixture Substances 0.000 description 83
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 78
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 54
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
• 229910001868 water Inorganic materials 0.000 description 41
• 238000006243 chemical reaction Methods 0.000 description 39
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 34
• 239000000047 product Substances 0.000 description 31
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 27
• 239000008363 phosphate buffer Substances 0.000 description 26
• 230000003115 biocidal effect Effects 0.000 description 25
• 239000008367 deionised water Substances 0.000 description 25
• 229910021641 deionized water Inorganic materials 0.000 description 25
• 239000002609 medium Substances 0.000 description 25
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
• 239000010410 layer Substances 0.000 description 22
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
• 239000011780 sodium chloride Substances 0.000 description 19
• 239000011541 reaction mixture Substances 0.000 description 18
• 239000000741 silica gel Substances 0.000 description 18
• 229910002027 silica gel Inorganic materials 0.000 description 18
• 235000019441 ethanol Nutrition 0.000 description 17
• 239000002904 solvent Substances 0.000 description 17
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
• 239000007858 starting material Substances 0.000 description 16
• 239000000725 suspension Substances 0.000 description 16
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
• 239000003921 oil Substances 0.000 description 15
• 235000019198 oils Nutrition 0.000 description 15
• 150000003952 β-lactams Chemical class 0.000 description 15
• 230000000903 blocking effect Effects 0.000 description 14
• 239000003153 chemical reaction reagent Substances 0.000 description 14
• 239000007787 solid Substances 0.000 description 14
• 238000003756 stirring Methods 0.000 description 14
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
• 239000012153 distilled water Substances 0.000 description 13
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
• 239000002253 acid Substances 0.000 description 12
• 239000003242 anti bacterial agent Substances 0.000 description 11
• 239000003795 chemical substances by application Substances 0.000 description 11
• 239000012141 concentrate Substances 0.000 description 11
• 239000000523 sample Substances 0.000 description 11
• 229940088710 antibiotic agent Drugs 0.000 description 10
• 235000008504 concentrate Nutrition 0.000 description 10
• 239000000706 filtrate Substances 0.000 description 10
• GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 10
• 239000011347 resin Substances 0.000 description 10
• 229920005989 resin Polymers 0.000 description 10
• 239000000872 buffer Substances 0.000 description 9
• 239000007788 liquid Substances 0.000 description 9
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 9
• 239000002808 molecular sieve Substances 0.000 description 9
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
• URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 9
• 229920001817 Agar Polymers 0.000 description 8
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
• 241000607132 Salmonella enterica subsp. enterica serovar Gallinarum Species 0.000 description 8
• 239000008272 agar Substances 0.000 description 8
• 150000001408 amides Chemical group 0.000 description 8
• 235000010633 broth Nutrition 0.000 description 8
• 239000007836 KH2PO4 Substances 0.000 description 7
• 239000008346 aqueous phase Substances 0.000 description 7
• ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 7
• RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 7
• 238000004128 high performance liquid chromatography Methods 0.000 description 7
• 235000019341 magnesium sulphate Nutrition 0.000 description 7
• 229910000402 monopotassium phosphate Inorganic materials 0.000 description 7
• 235000019796 monopotassium phosphate Nutrition 0.000 description 7
• GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 7
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
• UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 6
• 101150065749 Churc1 gene Proteins 0.000 description 6
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
• 235000000434 Melocanna baccifera Nutrition 0.000 description 6
• 241001497770 Melocanna baccifera Species 0.000 description 6
• PVCJKHHOXFKFRP-UHFFFAOYSA-N N-acetylethanolamine Chemical compound CC(=O)NCCO PVCJKHHOXFKFRP-UHFFFAOYSA-N 0.000 description 6
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
• 239000003513 alkali Substances 0.000 description 6
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 6
• IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 6
• 238000010790 dilution Methods 0.000 description 6
• 239000012895 dilution Substances 0.000 description 6
• 229910000396 dipotassium phosphate Inorganic materials 0.000 description 6
• 235000019797 dipotassium phosphate Nutrition 0.000 description 6
• 238000000855 fermentation Methods 0.000 description 6
• 230000004151 fermentation Effects 0.000 description 6
• FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 6
• 238000005984 hydrogenation reaction Methods 0.000 description 6
• 230000007062 hydrolysis Effects 0.000 description 6
• 238000006460 hydrolysis reaction Methods 0.000 description 6
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
• 241000894006 Bacteria Species 0.000 description 5
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 5
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
• 150000008065 acid anhydrides Chemical class 0.000 description 5
• 150000008064 anhydrides Chemical class 0.000 description 5
• 239000002585 base Substances 0.000 description 5
• 239000012267 brine Substances 0.000 description 5
• 238000004587 chromatography analysis Methods 0.000 description 5
• 239000003814 drug Substances 0.000 description 5
• 230000000694 effects Effects 0.000 description 5
• 150000004820 halides Chemical class 0.000 description 5
• 230000014759 maintenance of location Effects 0.000 description 5
• 239000000463 material Substances 0.000 description 5
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
• 239000012071 phase Substances 0.000 description 5
• 239000000843 powder Substances 0.000 description 5
• 238000012746 preparative thin layer chromatography Methods 0.000 description 5
• 230000035484 reaction time Effects 0.000 description 5
• 238000010992 reflux Methods 0.000 description 5
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
• 238000004809 thin layer chromatography Methods 0.000 description 5
• KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
• 241001453268 Comamonas terrigena Species 0.000 description 4
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
• 244000285963 Kluyveromyces fragilis Species 0.000 description 4
• 235000014663 Kluyveromyces fragilis Nutrition 0.000 description 4
• 240000004808 Saccharomyces cerevisiae Species 0.000 description 4
• 239000004480 active ingredient Substances 0.000 description 4
• 238000005917 acylation reaction Methods 0.000 description 4
• MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 4
• 235000011089 carbon dioxide Nutrition 0.000 description 4
• 239000012230 colorless oil Substances 0.000 description 4
• 239000012043 crude product Substances 0.000 description 4
• 238000010586 diagram Methods 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
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