NO763546L

NO763546L -

Info

Publication number: NO763546L
Authority: NO; Norway
Prior art keywords: acid; starting material; water; salts; sodium
Prior art date: 1971-01-20

Application number

NO763546A

Other languages

English (en)

Norwegian (no)

Inventor

A Furlenmeier

P Quitt

K Vogler

P Lanz

Original Assignee

Hoffmann La Roche

Priority date

1971-01-20

Filing date

1976-10-18

Publication date

1972-07-21

1971-01-20 Priority claimed from CH84871A external-priority patent/CH580631A5/xx

1972-07-21 Publication of NO763546L publication Critical patent/NO763546L/no

1976-10-18 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1976-10-18 Priority to NO763546A priority Critical patent/NO763546L/no

Links

-1 ok so Chemical group 0.000 claims description 83
238000002360 preparation method Methods 0.000 claims description 32
150000001875 compounds Chemical class 0.000 claims description 24
150000003839 salts Chemical class 0.000 claims description 23
239000011734 sodium Substances 0.000 claims description 6
229910052708 sodium Inorganic materials 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
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 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
125000003373 pyrazinyl group Chemical group 0.000 claims description 4
125000002252 acyl group Chemical group 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
229940049954 penicillin Drugs 0.000 claims description 3
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
230000003115 biocidal effect Effects 0.000 claims description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
125000001041 indolyl group Chemical group 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
125000000168 pyrrolyl group Chemical group 0.000 claims description 2
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 111
239000007858 starting material Substances 0.000 description 80
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 59
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 57
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 55
239000000243 solution Substances 0.000 description 47
235000019439 ethyl acetate Nutrition 0.000 description 37
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 29
239000002253 acid Substances 0.000 description 27
FCPVYOBCFFNJFS-LQDWTQKMSA-M benzylpenicillin sodium Chemical compound [Na+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)CC1=CC=CC=C1 FCPVYOBCFFNJFS-LQDWTQKMSA-M 0.000 description 23
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
238000000354 decomposition reaction Methods 0.000 description 21
238000003756 stirring Methods 0.000 description 17
238000003776 cleavage reaction Methods 0.000 description 16
230000007017 scission Effects 0.000 description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 description 11
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
238000004519 manufacturing process Methods 0.000 description 11
239000003921 oil Substances 0.000 description 11
235000019198 oils Nutrition 0.000 description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
238000001035 drying Methods 0.000 description 10
239000011736 potassium bicarbonate Substances 0.000 description 10
229910000028 potassium bicarbonate Inorganic materials 0.000 description 10
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
239000003208 petroleum Substances 0.000 description 9
235000015497 potassium bicarbonate Nutrition 0.000 description 9
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical group CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
239000000203 mixture Substances 0.000 description 8
238000005406 washing Methods 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
238000001704 evaporation Methods 0.000 description 7
230000008020 evaporation Effects 0.000 description 7
229910052943 magnesium sulfate Inorganic materials 0.000 description 7
235000019341 magnesium sulphate Nutrition 0.000 description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
150000007513 acids Chemical class 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
239000000284 extract Substances 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
125000006239 protecting group Chemical group 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
239000002904 solvent Substances 0.000 description 4
OSBDCZOPWJXASO-SNVBAGLBSA-N (2r)-4-methyl-2-(pyridine-3-carbonyloxy)pentanoic acid Chemical compound CC(C)C[C@H](C(O)=O)OC(=O)C1=CC=CN=C1 OSBDCZOPWJXASO-SNVBAGLBSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
229930182555 Penicillin Natural products 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
LNYCLASVFGVAII-GFCCVEGCSA-N benzyl (2r)-2-hydroxy-4-methylpentanoate Chemical compound CC(C)C[C@@H](O)C(=O)OCC1=CC=CC=C1 LNYCLASVFGVAII-GFCCVEGCSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 3
239000005457 ice water Substances 0.000 description 3
238000000034 method Methods 0.000 description 3
239000011591 potassium Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
JJIIJBVSYHWBIT-MRVPVSSYSA-N (2r)-2-(5-bromofuran-2-carbonyl)oxy-4-methylpentanoic acid Chemical compound CC(C)C[C@H](C(O)=O)OC(=O)C1=CC=C(Br)O1 JJIIJBVSYHWBIT-MRVPVSSYSA-N 0.000 description 2
AJVAZBQHVSBCBG-CQSZACIVSA-N (2r)-2-(7-chloroquinoline-4-carbonyl)oxy-4-methylpentanoic acid Chemical compound ClC1=CC=C2C(C(=O)O[C@H](CC(C)C)C(O)=O)=CC=NC2=C1 AJVAZBQHVSBCBG-CQSZACIVSA-N 0.000 description 2
MKNISDJDYYUMBA-LLVKDONJSA-N (2r)-2-[5-(methoxymethyl)furan-2-carbonyl]oxy-4-methylpentanoic acid Chemical compound COCC1=CC=C(C(=O)O[C@H](CC(C)C)C(O)=O)O1 MKNISDJDYYUMBA-LLVKDONJSA-N 0.000 description 2
UIGMHTGIJAVDDB-MRVPVSSYSA-N (2r)-4-methyl-2-(1,2-oxazole-3-carbonyloxy)pentanoic acid Chemical compound CC(C)C[C@H](C(O)=O)OC(=O)C=1C=CON=1 UIGMHTGIJAVDDB-MRVPVSSYSA-N 0.000 description 2
ZLGVTTNXFUCVGH-MRVPVSSYSA-N (2r)-4-methyl-2-(1,3-oxazole-4-carbonyloxy)pentanoic acid Chemical compound CC(C)C[C@H](C(O)=O)OC(=O)C1=COC=N1 ZLGVTTNXFUCVGH-MRVPVSSYSA-N 0.000 description 2
NEDVPRVZCTXJIH-SECBINFHSA-N (2r)-4-methyl-2-(1-methylimidazole-4-carbonyl)oxypentanoic acid Chemical compound CC(C)C[C@H](C(O)=O)OC(=O)C1=CN(C)C=N1 NEDVPRVZCTXJIH-SECBINFHSA-N 0.000 description 2
SQEGGWYFZFLOLL-SNVBAGLBSA-N (2r)-4-methyl-2-(5-methylfuran-2-carbonyl)oxypentanoic acid Chemical compound CC(C)C[C@H](C(O)=O)OC(=O)C1=CC=C(C)O1 SQEGGWYFZFLOLL-SNVBAGLBSA-N 0.000 description 2
GDGNUCAOGKIUOX-SNVBAGLBSA-N (2r)-4-methyl-2-(pyridine-4-carbonyloxy)pentanoic acid Chemical compound CC(C)C[C@H](C(O)=O)OC(=O)C1=CC=NC=C1 GDGNUCAOGKIUOX-SNVBAGLBSA-N 0.000 description 2
ZFVQSHMGJCZJHI-CQSZACIVSA-N (2r)-4-methyl-2-(quinoline-2-carbonyloxy)pentanoic acid Chemical compound C1=CC=CC2=NC(C(=O)O[C@H](CC(C)C)C(O)=O)=CC=C21 ZFVQSHMGJCZJHI-CQSZACIVSA-N 0.000 description 2
ARBSULDLPGESAS-CQSZACIVSA-N (2r)-4-methyl-2-(quinoline-4-carbonyloxy)pentanoic acid Chemical compound C1=CC=C2C(C(=O)O[C@H](CC(C)C)C(O)=O)=CC=NC2=C1 ARBSULDLPGESAS-CQSZACIVSA-N 0.000 description 2
SSLARYBQMAXWKL-VIFPVBQESA-N (2s)-2-(furan-2-carbonyloxy)-4-methylpentanoic acid Chemical compound CC(C)C[C@@H](C(O)=O)OC(=O)C1=CC=CO1 SSLARYBQMAXWKL-VIFPVBQESA-N 0.000 description 2
OHSLCKWYVFUXIW-UHFFFAOYSA-N (4-methyl-1-oxo-1-phenylmethoxypentan-2-yl) pyridine-4-carboxylate Chemical compound C=1C=CC=CC=1COC(=O)C(CC(C)C)OC(=O)C1=CC=NC=C1 OHSLCKWYVFUXIW-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
BSEHCAXAIKBAQF-UHFFFAOYSA-N 2-(pyridine-4-carbonyloxy)pentanoic acid Chemical compound CCCC(C(O)=O)OC(=O)C1=CC=NC=C1 BSEHCAXAIKBAQF-UHFFFAOYSA-N 0.000 description 2
SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 2
YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 2
GDGNUCAOGKIUOX-UHFFFAOYSA-N 4-methyl-2-(pyridine-4-carbonyloxy)pentanoic acid Chemical compound CC(C)CC(C(O)=O)OC(=O)C1=CC=NC=C1 GDGNUCAOGKIUOX-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 2
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
WEKSWPWYOSZOCB-MRXNPFEDSA-N [(2r)-4-methyl-1-oxo-1-phenylmethoxypentan-2-yl] furan-2-carboxylate Chemical compound O([C@H](CC(C)C)C(=O)OCC=1C=CC=CC=1)C(=O)C1=CC=CO1 WEKSWPWYOSZOCB-MRXNPFEDSA-N 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
239000003708 ampul Substances 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
150000001540 azides Chemical class 0.000 description 2
239000002585 base Substances 0.000 description 2
IYMAUEAFOBSGCY-UHFFFAOYSA-N benzene;sulfurochloridic acid Chemical compound OS(Cl)(=O)=O.C1=CC=CC=C1 IYMAUEAFOBSGCY-UHFFFAOYSA-N 0.000 description 2
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
229940073608 benzyl chloride Drugs 0.000 description 2
239000002775 capsule Substances 0.000 description 2
150000001718 carbodiimides Chemical class 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
125000004185 ester group Chemical group 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
150000002367 halogens Chemical group 0.000 description 2
TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
229910000510 noble metal Inorganic materials 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000007921 spray Substances 0.000 description 2
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 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
OFEMXQVRZIAUCU-SNVBAGLBSA-N (2r)-2-(1,5-dimethylpyrazole-3-carbonyl)oxy-4-methylpentanoic acid Chemical compound CC(C)C[C@H](C(O)=O)OC(=O)C=1C=C(C)N(C)N=1 OFEMXQVRZIAUCU-SNVBAGLBSA-N 0.000 description 1
VVPWFARZBKNXDJ-GFCCVEGCSA-N (2r)-2-(1-benzofuran-2-carbonyloxy)-4-methylpentanoic acid Chemical compound C1=CC=C2OC(C(=O)O[C@H](CC(C)C)C(O)=O)=CC2=C1 VVPWFARZBKNXDJ-GFCCVEGCSA-N 0.000 description 1
TVSULVYVZMXTLT-LLVKDONJSA-N (2r)-2-(2,4-dimethylpyrimidine-5-carbonyl)oxy-4-methylpentanoic acid Chemical compound CC(C)C[C@H](C(O)=O)OC(=O)C1=CN=C(C)N=C1C TVSULVYVZMXTLT-LLVKDONJSA-N 0.000 description 1
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