NO124162B - - Google Patents

Info

Publication number

NO124162B

NO124162B NO96571A NO96571A NO124162B NO 124162 B NO124162 B NO 124162B NO 96571 A NO96571 A NO 96571A NO 96571 A NO96571 A NO 96571A NO 124162 B NO124162 B NO 124162B

Authority

NO

Norway

Prior art keywords

carbon atoms

thionyl chloride

formula

production

acid addition

Prior art date

1965-02-08

Links

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• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 18
• 125000004432 carbon atom Chemical group C* 0.000 claims description 10
• 150000001875 compounds Chemical class 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 239000002253 acid Substances 0.000 claims description 5
• 238000000034 method Methods 0.000 claims description 5
• 150000003839 salts Chemical class 0.000 claims description 5
• 239000007858 starting material Substances 0.000 claims description 4
• OJMMVQQUTAEWLP-KIDUDLJLSA-N lincomycin Chemical class CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@@H](C)O)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 OJMMVQQUTAEWLP-KIDUDLJLSA-N 0.000 claims description 3
• 125000000217 alkyl group Chemical group 0.000 claims description 2
• 125000002947 alkylene group Chemical group 0.000 claims description 2
• 125000001118 alkylidene group Chemical group 0.000 claims description 2
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
• 229910052739 hydrogen Inorganic materials 0.000 claims description 2
• 239000001257 hydrogen Substances 0.000 claims description 2
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
• LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
• 229910052757 nitrogen Inorganic materials 0.000 description 2
• 239000011541 reaction mixture Substances 0.000 description 2
• 239000007787 solid Substances 0.000 description 2
• 238000003756 stirring Methods 0.000 description 2
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
• ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical class OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 1
• OJMMVQQUTAEWLP-UHFFFAOYSA-N Lincomycin Natural products CN1CC(CCC)CC1C(=O)NC(C(C)O)C1C(O)C(O)C(O)C(SC)O1 OJMMVQQUTAEWLP-UHFFFAOYSA-N 0.000 description 1
• 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
• 238000004458 analytical method Methods 0.000 description 1
• 238000006243 chemical reaction Methods 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 230000007062 hydrolysis Effects 0.000 description 1
• 238000006460 hydrolysis reaction Methods 0.000 description 1
• POUMFISTNHIPTI-BOMBIWCESA-N hydron;(2s,4r)-n-[(1r,2r)-2-hydroxy-1-[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide;chloride Chemical compound Cl.CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@@H](C)O)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 POUMFISTNHIPTI-BOMBIWCESA-N 0.000 description 1
• 239000012442 inert solvent Substances 0.000 description 1
• 229960005287 lincomycin Drugs 0.000 description 1
• 229960001595 lincomycin hydrochloride Drugs 0.000 description 1
• 238000004949 mass spectrometry Methods 0.000 description 1
• 238000006386 neutralization reaction Methods 0.000 description 1
• 239000002904 solvent Substances 0.000 description 1
• 125000001424 substituent group Chemical group 0.000 description 1
• LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
• 239000000725 suspension Substances 0.000 description 1