JP2015509939A5 - - Google Patents

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Publication number

JP2015509939A5

JP2015509939A5 JP2014557781A JP2014557781A JP2015509939A5 JP 2015509939 A5 JP2015509939 A5 JP 2015509939A5 JP 2014557781 A JP2014557781 A JP 2014557781A JP 2014557781 A JP2014557781 A JP 2014557781A JP 2015509939 A5 JP2015509939 A5 JP 2015509939A5

Authority

JP

Japan

Prior art keywords

formula

compound

group

alkyl

organic solvent

Prior art date

2013-02-14

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.)

Granted

Links

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• 238000000034 method Methods 0.000 claims 32
• 150000001875 compounds Chemical class 0.000 claims 30
• 125000000217 alkyl group Chemical group 0.000 claims 8
• 239000003960 organic solvent Substances 0.000 claims 8
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 6
• 125000003545 alkoxy group Chemical group 0.000 claims 6
• 229910052736 halogen Inorganic materials 0.000 claims 6
• 150000002367 halogens Chemical class 0.000 claims 6
• 239000000203 mixture Substances 0.000 claims 6
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 6
• 229910052739 hydrogen Inorganic materials 0.000 claims 5
• 239000001257 hydrogen Substances 0.000 claims 5
• 230000001590 oxidative effect Effects 0.000 claims 5
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 4
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 4
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 4
• 150000002431 hydrogen Chemical class 0.000 claims 4
• 239000007800 oxidant agent Substances 0.000 claims 4
• 230000003647 oxidation Effects 0.000 claims 4
• 238000007254 oxidation reaction Methods 0.000 claims 4
• 239000002904 solvent Substances 0.000 claims 4
• PAQZWJGSJMLPMG-UHFFFAOYSA-N 2,4,6-tripropyl-1,3,5,2$l^{5},4$l^{5},6$l^{5}-trioxatriphosphinane 2,4,6-trioxide Chemical group CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 PAQZWJGSJMLPMG-UHFFFAOYSA-N 0.000 claims 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
• 239000004367 Lipase Substances 0.000 claims 3
• 102000004882 Lipase Human genes 0.000 claims 3
• 108090001060 Lipase Proteins 0.000 claims 3
• 239000005708 Sodium hypochlorite Substances 0.000 claims 3
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
• 235000019421 lipase Nutrition 0.000 claims 3
• UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 claims 3
• 229960002218 sodium chlorite Drugs 0.000 claims 3
• SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims 3
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims 2
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 2
• QYTDEUPAUMOIOP-UHFFFAOYSA-N TEMPO Chemical group CC1(C)CCCC(C)(C)N1[O] QYTDEUPAUMOIOP-UHFFFAOYSA-N 0.000 claims 2
• 150000001408 amides Chemical class 0.000 claims 2
• 150000001412 amines Chemical class 0.000 claims 2
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
• 229910052794 bromium Inorganic materials 0.000 claims 2
• 238000006243 chemical reaction Methods 0.000 claims 2
• 239000003638 chemical reducing agent Substances 0.000 claims 2
• 229910052801 chlorine Inorganic materials 0.000 claims 2
• 239000000460 chlorine Substances 0.000 claims 2
• 239000007822 coupling agent Substances 0.000 claims 2
• 229910052731 fluorine Inorganic materials 0.000 claims 2
• 239000011737 fluorine Substances 0.000 claims 2
• 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
• 150000004678 hydrides Chemical class 0.000 claims 2
• GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 claims 2
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
• VPAHTUQECJIGCK-UHFFFAOYSA-N (2-methylphenyl)sulfonyl 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S(=O)(=O)OS(=O)(=O)C1=CC=CC=C1C VPAHTUQECJIGCK-UHFFFAOYSA-N 0.000 claims 1
• HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 claims 1
• JXRGUPLJCCDGKG-UHFFFAOYSA-N 4-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(S(Cl)(=O)=O)C=C1 JXRGUPLJCCDGKG-UHFFFAOYSA-N 0.000 claims 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 1
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 239000012448 Lithium borohydride Substances 0.000 claims 1
• 239000012359 Methanesulfonyl chloride Substances 0.000 claims 1
• 241001661345 Moesziomyces antarcticus Species 0.000 claims 1
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
• XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims 1
• 230000002378 acidificating effect Effects 0.000 claims 1
• 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
• 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 1
• 125000004093 cyano group Chemical group *C#N 0.000 claims 1
• 150000008282 halocarbons Chemical class 0.000 claims 1
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
• 229910052740 iodine Inorganic materials 0.000 claims 1
• 239000011630 iodine Substances 0.000 claims 1
• -1 lithium triethylborohydride Chemical compound 0.000 claims 1
• IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 claims 1
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims 1
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
• 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
• 150000003230 pyrimidines Chemical class 0.000 claims 1
• 238000010791 quenching Methods 0.000 claims 1
• 230000000171 quenching effect Effects 0.000 claims 1
• 229910052708 sodium Inorganic materials 0.000 claims 1
• 239000011734 sodium Substances 0.000 claims 1
• 238000003756 stirring Methods 0.000 claims 1
• 125000001424 substituent group Chemical group 0.000 claims 1
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
• 0 *[C@](COc1cnc(*)nc1*)(C1)[C@@]1C=O Chemical compound *[C@](COc1cnc(*)nc1*)(C1)[C@@]1C=O 0.000 description 1
• HGJBPBRHSNPZSW-UHFFFAOYSA-N O=C1OCC(C2)C12[AlH2] Chemical compound O=C1OCC(C2)C12[AlH2] HGJBPBRHSNPZSW-UHFFFAOYSA-N 0.000 description 1