BE502258A - - Google Patents
Info
- Publication number
- BE502258A BE502258A BE502258DA BE502258A BE 502258 A BE502258 A BE 502258A BE 502258D A BE502258D A BE 502258DA BE 502258 A BE502258 A BE 502258A
- Authority
- BE
- Belgium
- Prior art keywords
- serine
- phenyl
- threo
- quinine
- antipode
- Prior art date
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 59
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 claims description 58
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 30
- 235000001258 Cinchona calisaya Nutrition 0.000 claims description 21
- 241000434299 Cinchona officinalis Species 0.000 claims description 21
- 229960000948 Quinine Drugs 0.000 claims description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
- 239000002585 base Substances 0.000 claims description 20
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 16
- 239000011780 sodium chloride Substances 0.000 claims description 16
- 239000000047 product Substances 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 14
- VHVGNTVUSQUXPS-YUMQZZPRSA-N L-threo-3-phenylserine zwitterion Chemical compound [O-]C(=O)[C@@H]([NH3+])[C@@H](O)C1=CC=CC=C1 VHVGNTVUSQUXPS-YUMQZZPRSA-N 0.000 claims description 12
- 239000003513 alkali Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 12
- 150000001413 amino acids Chemical class 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 8
- 238000001953 recrystallisation Methods 0.000 claims description 8
- 238000000926 separation method Methods 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 6
- 239000011707 mineral Substances 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 5
- 230000005591 charge neutralization Effects 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 238000001640 fractional crystallisation Methods 0.000 claims description 5
- 230000001264 neutralization Effects 0.000 claims description 5
- 238000006386 neutralization reaction Methods 0.000 claims description 5
- 239000002244 precipitate Substances 0.000 claims description 5
- 159000000000 sodium salts Chemical class 0.000 claims description 5
- 239000001096 (4-ethenyl-1-azabicyclo[2.2.2]octan-7-yl)-(6-methoxyquinolin-4-yl)methanol hydrochloride Substances 0.000 claims description 4
- LBSFSRMTJJPTCW-DSXUQNDKSA-N (R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol;hydrochloride Chemical compound Cl.C([C@H]([C@H](C1)C=C)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LBSFSRMTJJPTCW-DSXUQNDKSA-N 0.000 claims description 4
- 229960001811 Quinine Hydrochloride Drugs 0.000 claims description 4
- 238000007792 addition Methods 0.000 claims description 4
- 239000012141 concentrate Substances 0.000 claims description 4
- 239000012452 mother liquor Substances 0.000 claims description 4
- VHVGNTVUSQUXPS-GVHYBUMESA-N (2R)-2-amino-3-hydroxy-3-phenylpropanoic acid Chemical compound OC(=O)[C@H](N)C(O)C1=CC=CC=C1 VHVGNTVUSQUXPS-GVHYBUMESA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000000706 filtrate Substances 0.000 claims description 3
- 238000007127 saponification reaction Methods 0.000 claims description 3
- 239000008346 aqueous phase Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 239000012071 phase Substances 0.000 claims 2
- MTCFGRXMJLQNBG-UWTATZPHSA-N D-serine Chemical compound OC[C@@H](N)C(O)=O MTCFGRXMJLQNBG-UWTATZPHSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 238000002844 melting Methods 0.000 description 14
- 230000003287 optical Effects 0.000 description 13
- 238000010438 heat treatment Methods 0.000 description 10
- VHVGNTVUSQUXPS-JAMMHHFISA-N L-Threo-3-Phenylserine Chemical compound OC(=O)[C@@H](N)C(O)C1=CC=CC=C1 VHVGNTVUSQUXPS-JAMMHHFISA-N 0.000 description 9
- 238000002425 crystallisation Methods 0.000 description 9
- 230000005712 crystallization Effects 0.000 description 9
- 238000000354 decomposition reaction Methods 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229960000583 Acetic Acid Drugs 0.000 description 3
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 150000003862 amino acid derivatives Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- HUMNYLRZRPPJDN-UHFFFAOYSA-N Benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 239000004473 Threonine Substances 0.000 description 2
- -1 acetyl compound Chemical class 0.000 description 2
- 230000001476 alcoholic Effects 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propanol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 125000003410 quininyl group Chemical group 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 229960002898 threonine Drugs 0.000 description 2
- VHVGNTVUSQUXPS-SFYZADRCSA-N (2R,3S)-2-amino-3-hydroxy-3-phenylpropanoic acid Chemical compound OC(=O)[C@H](N)[C@@H](O)C1=CC=CC=C1 VHVGNTVUSQUXPS-SFYZADRCSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 235000019749 Dry matter Nutrition 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 229940095076 benzaldehyde Drugs 0.000 description 1
- ABNDFSOIUFLJAH-UHFFFAOYSA-N benzyl thiocyanate Chemical compound N#CSCC1=CC=CC=C1 ABNDFSOIUFLJAH-UHFFFAOYSA-N 0.000 description 1
- 235000012970 cakes Nutrition 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005947 deacylation reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 159000000011 group IA salts Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- QDHHCQZDFGDHMP-UHFFFAOYSA-N monochloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000003472 neutralizing Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atoms Chemical group N* 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000035943 smell Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE502258A true BE502258A (xx) |
Family
ID=143818
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE502258D BE502258A (xx) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE502258A (xx) |
-
0
- BE BE502258D patent/BE502258A/fr unknown
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