UA79830C2 - Tricyclic compounds (variants), process for the preparation thereof (variants), pharmaceutical composition containing thereof, process for the preparation of pharmaceutical composition, method for inhibiting hiv-integrase using mentioned compounds, method for treatment hiv-infection or treatment of aids or arc using mentioned compounds - Google Patents

Info

Publication number

UA79830C2

UA79830C2 UAA200504480A UA2005004480A UA79830C2 UA 79830 C2 UA79830 C2 UA 79830C2 UA A200504480 A UAA200504480 A UA A200504480A UA 2005004480 A UA2005004480 A UA 2005004480A UA 79830 C2 UA79830 C2 UA 79830C2

Authority

UA

Ukraine

Prior art keywords

substituted

compound according

phosphonate

group

alkyl

Prior art date

2002-10-16

Links

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• Global Dossier
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• 150000001875 compounds Chemical class 0.000 title claims abstract description 297
• 238000000034 method Methods 0.000 title claims abstract description 247
• 108010002459 HIV Integrase Proteins 0.000 title claims abstract description 17
• 230000002401 inhibitory effect Effects 0.000 title claims description 17
• 239000008194 pharmaceutical composition Substances 0.000 title claims description 14
• 208000031886 HIV Infections Diseases 0.000 title claims description 9
• 208000037357 HIV infectious disease Diseases 0.000 title claims description 4
• 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 title claims description 4
• 238000002360 preparation method Methods 0.000 title description 63
• 230000008569 process Effects 0.000 title description 6
• 239000000651 prodrug Substances 0.000 claims abstract description 100
• 229940002612 prodrug Drugs 0.000 claims abstract description 100
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 96
• 125000003118 aryl group Chemical group 0.000 claims abstract description 80
• 125000001424 substituent group Chemical group 0.000 claims abstract description 28
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
• 125000006413 ring segment Chemical group 0.000 claims abstract description 16
• UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 227
• -1 polyethyleneoxy Polymers 0.000 claims description 227
• 238000006243 chemical reaction Methods 0.000 claims description 225
• 150000002148 esters Chemical class 0.000 claims description 73
• ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 68
• 150000001412 amines Chemical class 0.000 claims description 61
• 229920006395 saturated elastomer Polymers 0.000 claims description 55
• 125000002947 alkylene group Chemical group 0.000 claims description 46
• 150000003839 salts Chemical class 0.000 claims description 38
• 125000000217 alkyl group Chemical group 0.000 claims description 37
• 229910052799 carbon Inorganic materials 0.000 claims description 36
• 239000003153 chemical reaction reagent Substances 0.000 claims description 36
• 125000003107 substituted aryl group Chemical group 0.000 claims description 36
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 31
• 229910019142 PO4 Inorganic materials 0.000 claims description 30
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 29
• 239000010452 phosphate Substances 0.000 claims description 29
• 125000006239 protecting group Chemical group 0.000 claims description 29
• 125000004122 cyclic group Chemical group 0.000 claims description 28
• 125000004432 carbon atom Chemical group C* 0.000 claims description 22
• 239000003795 chemical substances by application Substances 0.000 claims description 22
• 150000003951 lactams Chemical class 0.000 claims description 22
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims description 22
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
• 125000000623 heterocyclic group Chemical group 0.000 claims description 18
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 18
• IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 claims description 17
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 17
• 125000004450 alkenylene group Chemical group 0.000 claims description 15
• 125000003282 alkyl amino group Chemical group 0.000 claims description 15
• 150000007942 carboxylates Chemical class 0.000 claims description 15
• 241000282414 Homo sapiens Species 0.000 claims description 14
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 14
• 125000004419 alkynylene group Chemical group 0.000 claims description 14
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 13
• 125000003545 alkoxy group Chemical group 0.000 claims description 13
• KZNICNPSHKQLFF-UHFFFAOYSA-N dihydromaleimide Natural products O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 13
• 150000002596 lactones Chemical class 0.000 claims description 13
• 150000001350 alkyl halides Chemical class 0.000 claims description 12
• 230000003834 intracellular effect Effects 0.000 claims description 10
• 210000003819 peripheral blood mononuclear cell Anatomy 0.000 claims description 10
• 208000030507 AIDS Diseases 0.000 claims description 9
• 229960002317 succinimide Drugs 0.000 claims description 9
• 125000004429 atom Chemical group 0.000 claims description 8
• 125000002619 bicyclic group Chemical group 0.000 claims description 7
• 125000003003 spiro group Chemical group 0.000 claims description 7
• 239000002207 metabolite Substances 0.000 claims description 6
• 239000012453 solvate Substances 0.000 claims description 6
• 229940124530 sulfonamide Drugs 0.000 claims description 6
• 150000003456 sulfonamides Chemical class 0.000 claims description 6
• 125000004665 trialkylsilyl group Chemical group 0.000 claims description 6
• 229910052796 boron Inorganic materials 0.000 claims description 5
• 230000000694 effects Effects 0.000 claims description 5
• 229910052717 sulfur Inorganic materials 0.000 claims description 5
• UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims description 5
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
• 210000000265 leukocyte Anatomy 0.000 claims description 4
• 230000004048 modification Effects 0.000 claims description 4
• 238000012986 modification Methods 0.000 claims description 4
• 125000002950 monocyclic group Chemical group 0.000 claims description 4
• 239000002243 precursor Substances 0.000 claims description 4
• JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 claims description 3
• 229910020711 Co—Si Inorganic materials 0.000 claims description 3
• 241000124008 Mammalia Species 0.000 claims description 3
• 239000002955 immunomodulating agent Substances 0.000 claims description 3
• 229940121354 immunomodulator Drugs 0.000 claims description 3
• 150000002500 ions Chemical class 0.000 claims description 3
• 150000003457 sulfones Chemical class 0.000 claims description 3
• 150000003462 sulfoxides Chemical class 0.000 claims description 3
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
• 229940122440 HIV protease inhibitor Drugs 0.000 claims description 2
• 229940122313 Nucleoside reverse transcriptase inhibitor Drugs 0.000 claims description 2
• 229910052770 Uranium Inorganic materials 0.000 claims description 2
• ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 2
• 239000004030 hiv protease inhibitor Substances 0.000 claims description 2
• 230000002584 immunomodulator Effects 0.000 claims description 2
• 229940042402 non-nucleoside reverse transcriptase inhibitor Drugs 0.000 claims description 2
• 239000002726 nonnucleoside reverse transcriptase inhibitor Substances 0.000 claims description 2
• 239000003419 rna directed dna polymerase inhibitor Substances 0.000 claims description 2
• 150000008052 alkyl sulfonates Chemical class 0.000 claims 10
• 150000001356 alkyl thiols Chemical class 0.000 claims 10
• 125000004950 trifluoroalkyl group Chemical group 0.000 claims 9
• 239000003937 drug carrier Substances 0.000 claims 2
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
• DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 claims 1
• 241001116389 Aloe Species 0.000 claims 1
• 241000234435 Lilium Species 0.000 claims 1
• 241000256856 Vespidae Species 0.000 claims 1
• 150000004703 alkoxides Chemical class 0.000 claims 1
• 125000004849 alkoxymethyl group Chemical group 0.000 claims 1
• 235000011399 aloe vera Nutrition 0.000 claims 1
• 229960005475 antiinfective agent Drugs 0.000 claims 1
• 239000004599 antimicrobial Substances 0.000 claims 1
• 239000004330 calcium propionate Substances 0.000 claims 1
• 235000001159 dosh Nutrition 0.000 claims 1
• 244000245171 dosh Species 0.000 claims 1
• WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 1
• 150000002391 heterocyclic compounds Chemical class 0.000 claims 1
• 210000000003 hoof Anatomy 0.000 claims 1
• XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims 1
• 239000004309 nisin Substances 0.000 claims 1
• 238000012876 topography Methods 0.000 claims 1
• 239000000543 intermediate Substances 0.000 abstract description 41
• 229910052757 nitrogen Inorganic materials 0.000 abstract description 18
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 11
• 230000005764 inhibitory process Effects 0.000 abstract description 6
• 239000001257 hydrogen Substances 0.000 abstract description 5
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 4
• 150000002829 nitrogen Chemical class 0.000 abstract description 3
• 239000000047 product Substances 0.000 description 285
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 153
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 133
• 239000000203 mixture Substances 0.000 description 125
• 239000000243 solution Substances 0.000 description 124
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 121
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 90
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 87
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 79
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 79
• 230000000875 corresponding effect Effects 0.000 description 72
• 238000005481 NMR spectroscopy Methods 0.000 description 64
• 238000010511 deprotection reaction Methods 0.000 description 60
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 57
• 239000002585 base Substances 0.000 description 47
• 230000015572 biosynthetic process Effects 0.000 description 41
• 239000007787 solid Substances 0.000 description 41
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
• 229910052740 iodine Inorganic materials 0.000 description 40
• 125000003710 aryl alkyl group Chemical group 0.000 description 37
• 239000002904 solvent Substances 0.000 description 35
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 34
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
• 150000001408 amides Chemical class 0.000 description 33
• 235000019439 ethyl acetate Nutrition 0.000 description 33
• 239000004480 active ingredient Substances 0.000 description 32
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 31
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 30
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 30
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 29
• 238000004519 manufacturing process Methods 0.000 description 29
• 239000007858 starting material Substances 0.000 description 29
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 28
• 239000011541 reaction mixture Substances 0.000 description 28
• 239000002244 precipitate Substances 0.000 description 27
• 230000002829 reductive effect Effects 0.000 description 27
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 24
• 239000012043 crude product Substances 0.000 description 24
• 239000012299 nitrogen atmosphere Substances 0.000 description 23
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 22
• 239000003814 drug Substances 0.000 description 22
• AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 22
• 239000012044 organic layer Substances 0.000 description 21
• 238000004809 thin layer chromatography Methods 0.000 description 21
• 125000002015 acyclic group Chemical group 0.000 description 20
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 20
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 18
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 18
• 238000006460 hydrolysis reaction Methods 0.000 description 18
• 239000000126 substance Substances 0.000 description 18
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 18
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 17
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
• 150000001299 aldehydes Chemical class 0.000 description 17
• 230000007062 hydrolysis Effects 0.000 description 17
• 229910000027 potassium carbonate Inorganic materials 0.000 description 17
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
• 229940059260 amidate Drugs 0.000 description 16
• 150000002440 hydroxy compounds Chemical class 0.000 description 16
• 150000003009 phosphonic acids Chemical class 0.000 description 16
• 125000002924 primary amino group Chemical class [H]N([H])* 0.000 description 16
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• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 15
• 238000005859 coupling reaction Methods 0.000 description 15
• 229940079593 drug Drugs 0.000 description 15
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• 239000003054 catalyst Substances 0.000 description 14
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• 125000005647 linker group Chemical group 0.000 description 14
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• NPUKDXXFDDZOKR-LLVKDONJSA-N etomidate Chemical compound CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1 NPUKDXXFDDZOKR-LLVKDONJSA-N 0.000 description 13
• 239000003921 oil Substances 0.000 description 13
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• 241000725303 Human immunodeficiency virus Species 0.000 description 12
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• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 12
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• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 12
• 235000021317 phosphate Nutrition 0.000 description 12
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• 108020004414 DNA Proteins 0.000 description 11
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• 125000000524 functional group Chemical group 0.000 description 11
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• 238000006751 Mitsunobu reaction Methods 0.000 description 10
• 150000001721 carbon Chemical group 0.000 description 10
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
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• 239000012442 inert solvent Substances 0.000 description 10
• 239000003960 organic solvent Substances 0.000 description 10
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 10
• 238000010992 reflux Methods 0.000 description 10
• 238000006467 substitution reaction Methods 0.000 description 10
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• 125000004185 ester group Chemical group 0.000 description 9
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• 125000005842 heteroatom Chemical group 0.000 description 9
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
• 239000007788 liquid Substances 0.000 description 9
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• 229910052763 palladium Inorganic materials 0.000 description 9
• 150000002989 phenols Chemical class 0.000 description 9
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 9
• 239000003495 polar organic solvent Substances 0.000 description 9
• 239000000843 powder Substances 0.000 description 9
• PFFIDZXUXFLSSR-UHFFFAOYSA-N 1-methyl-N-[2-(4-methylpentan-2-yl)-3-thienyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound S1C=CC(NC(=O)C=2C(=NN(C)C=2)C(F)(F)F)=C1C(C)CC(C)C PFFIDZXUXFLSSR-UHFFFAOYSA-N 0.000 description 8
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
• 150000001336 alkenes Chemical class 0.000 description 8
• 239000012298 atmosphere Substances 0.000 description 8
• LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 8
• 235000012907 honey Nutrition 0.000 description 8
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• 239000010410 layer Substances 0.000 description 8
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 8
• 239000012074 organic phase Substances 0.000 description 8
• 239000002798 polar solvent Substances 0.000 description 8
• 238000006722 reduction reaction Methods 0.000 description 8
• KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 7
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• 108010061833 Integrases Proteins 0.000 description 7
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
• 230000009471 action Effects 0.000 description 7
• 238000005804 alkylation reaction Methods 0.000 description 7
• 150000007854 aminals Chemical class 0.000 description 7
• 238000004458 analytical method Methods 0.000 description 7
• 150000008064 anhydrides Chemical class 0.000 description 7
• UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 7
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