BE412099A - - Google Patents

Info

Publication number

BE412099A

BE412099A BE412099DA BE412099A BE 412099 A BE412099 A BE 412099A BE 412099D A BE412099D A BE 412099DA BE 412099 A BE412099 A BE 412099A

Authority

BE

Belgium

Prior art keywords

hydrolysis

acid

ether

water

desc

Prior art date

Links

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• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
• 239000003795 chemical substances by application Substances 0.000 claims description 7
• 230000007062 hydrolysis Effects 0.000 claims description 6
• 238000006460 hydrolysis reaction Methods 0.000 claims description 6
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
• 239000002253 acid Substances 0.000 claims description 3
• 230000002378 acidificating effect Effects 0.000 claims description 2
• 238000000034 method Methods 0.000 claims description 2
• 239000003960 organic solvent Substances 0.000 claims description 2
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 3
• 235000006408 oxalic acid Nutrition 0.000 claims 1
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical class O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
• 150000002576 ketones Chemical class 0.000 description 6
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
• 238000002844 melting Methods 0.000 description 4
• 230000008018 melting Effects 0.000 description 4
• 230000003647 oxidation Effects 0.000 description 4
• 238000007254 oxidation reaction Methods 0.000 description 4
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
• 239000007857 degradation product Substances 0.000 description 3
• 239000007800 oxidant agent Substances 0.000 description 3
• 239000000047 product Substances 0.000 description 3
• 150000007659 semicarbazones Chemical class 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
• 239000003613 bile acid Substances 0.000 description 2
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
• 230000003301 hydrolyzing effect Effects 0.000 description 2
• -1 ketone compounds Chemical class 0.000 description 2
• 239000000155 melt Substances 0.000 description 2
• 230000007935 neutral effect Effects 0.000 description 2
• 238000002360 preparation method Methods 0.000 description 2
• 229930193551 sterin Natural products 0.000 description 2
• DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
• LQJWJTSOPATCCR-UHFFFAOYSA-N O=C=O.CCC(O)=O Chemical compound O=C=O.CCC(O)=O LQJWJTSOPATCCR-UHFFFAOYSA-N 0.000 description 1
• KNDUBESZKGHTSA-CJVRWNGOSA-N [(3r,5s,8r,9s,10s,13s,14s)-10,13-dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl] benzoate Chemical compound O([C@H]1C[C@@H]2CC[C@@H]3[C@@H]([C@]2(CC1)C)CC[C@]1([C@H]3CCC1=O)C)C(=O)C1=CC=CC=C1 KNDUBESZKGHTSA-CJVRWNGOSA-N 0.000 description 1
• 229960000583 acetic acid Drugs 0.000 description 1
• 159000000032 aromatic acids Chemical class 0.000 description 1
• 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
• 230000015572 biosynthetic process Effects 0.000 description 1
• 239000003153 chemical reaction reagent Substances 0.000 description 1
• KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
• 230000001684 chronic effect Effects 0.000 description 1
• 238000002425 crystallisation Methods 0.000 description 1
• 230000008025 crystallization Effects 0.000 description 1
• 125000004122 cyclic group Chemical group 0.000 description 1
• QYIXCDOBOSTCEI-FBVYSKEZSA-N epidihydrocholesterin Chemical compound C([C@@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CCCC(C)C)[C@@]2(C)CC1 QYIXCDOBOSTCEI-FBVYSKEZSA-N 0.000 description 1
• 125000001033 ether group Chemical group 0.000 description 1
• 230000008020 evaporation Effects 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
• 239000012362 glacial acetic acid Substances 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
• 150000002923 oximes Chemical class 0.000 description 1
• 239000003208 petroleum Substances 0.000 description 1
• 235000019260 propionic acid Nutrition 0.000 description 1
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• 238000007127 saponification reaction Methods 0.000 description 1
• 229920006395 saturated elastomer Polymers 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 239000000126 substance Substances 0.000 description 1
• 230000009466 transformation Effects 0.000 description 1
• 238000005292 vacuum distillation Methods 0.000 description 1