SU533334A3 - Способ получени стереоизомеров 1-/11-(о-хлорбензил)-21 -пиррил/-2-ди-втор-бутиламиноэтанола - Google Patents
Способ получени стереоизомеров 1-/11-(о-хлорбензил)-21 -пиррил/-2-ди-втор-бутиламиноэтанолаInfo
- Publication number
- SU533334A3 SU533334A3 SU1848312A SU1848312A SU533334A3 SU 533334 A3 SU533334 A3 SU 533334A3 SU 1848312 A SU1848312 A SU 1848312A SU 1848312 A SU1848312 A SU 1848312A SU 533334 A3 SU533334 A3 SU 533334A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- sec
- chlorobenzyl
- pyrryl
- ethanol
- butylamino
- Prior art date
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title description 7
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 title description 5
- 238000000034 method Methods 0.000 title description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 8
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- -1 chloro - Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000004803 chlorobenzyl group Chemical group 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- HOPOOSWMGTVLDJ-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]-1H-pyrrole Chemical compound ClC1=C(CC2=CC=CN2)C=CC=C1 HOPOOSWMGTVLDJ-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 101100120289 Drosophila melanogaster Flo1 gene Proteins 0.000 description 1
- 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 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N N-butylamine Natural products CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- OBASDBHRXUCXKQ-UHFFFAOYSA-N [F].[Br] Chemical compound [F].[Br] OBASDBHRXUCXKQ-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 210000000867 larynx Anatomy 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000010413 mother solution Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- JBJWASZNUJCEKT-UHFFFAOYSA-M sodium;hydroxide;hydrate Chemical compound O.[OH-].[Na+] JBJWASZNUJCEKT-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- SSTZGACKDAVIGZ-UHFFFAOYSA-N sulfanium;bromide Chemical compound [SH3+].[Br-] SSTZGACKDAVIGZ-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/337—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT3058871 | 1971-10-30 | ||
| IT3058671 | 1971-10-30 | ||
| IT3058771 | 1971-10-30 | ||
| IT3058571 | 1971-10-30 | ||
| IT2656472A IT1044847B (it) | 1972-07-04 | 1972-07-04 | Benzil pirril aminoetanolo dotato di attivita antagonista nei con fronti della capacita ad indurre dipendenza fisica di composti dotati di attivita analgesica |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU533334A3 true SU533334A3 (ru) | 1976-10-25 |
Family
ID=27517845
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1848312A SU533334A3 (ru) | 1971-10-30 | 1972-10-30 | Способ получени стереоизомеров 1-/11-(о-хлорбензил)-21 -пиррил/-2-ди-втор-бутиламиноэтанола |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US3857857A (enExample) |
| JP (1) | JPS5418247B2 (enExample) |
| AR (1) | AR194281A1 (enExample) |
| AU (1) | AU475877B2 (enExample) |
| BE (1) | BE790747A (enExample) |
| CA (1) | CA974245A (enExample) |
| CH (1) | CH583194A5 (enExample) |
| CS (1) | CS174859B2 (enExample) |
| DE (1) | DE2253150C3 (enExample) |
| DK (1) | DK138642B (enExample) |
| FI (1) | FI54105C (enExample) |
| FR (1) | FR2158056B1 (enExample) |
| GB (1) | GB1405148A (enExample) |
| IE (1) | IE36907B1 (enExample) |
| IL (1) | IL40665A (enExample) |
| NL (1) | NL178073C (enExample) |
| NO (1) | NO137784C (enExample) |
| SE (1) | SE387940B (enExample) |
| SU (1) | SU533334A3 (enExample) |
| YU (1) | YU267272A (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE848465A (fr) * | 1976-11-18 | 1977-03-16 | Stereo-isomeres de 1-(1'-benzyl-2' pyrryl)-2-disec.butylaminoethanols a activite analgesique et preparations pharmaceutiques qui les contiennent | |
| EP0342613B1 (en) * | 1988-05-20 | 1992-11-11 | ZAMBON GROUP S.p.A. | Compounds with central analgesic activity, process for their preparation and pharmaceutical compositions containing them |
| AU2009239778B2 (en) * | 2008-04-24 | 2014-03-13 | F2G Ltd | Pyrrole antifungal agents |
| MX2017006447A (es) | 2014-11-21 | 2018-01-30 | F2G Ltd | Agentes antifungicos. |
| GB201609222D0 (en) | 2016-05-25 | 2016-07-06 | F2G Ltd | Pharmaceutical formulation |
| US11819503B2 (en) | 2019-04-23 | 2023-11-21 | F2G Ltd | Method of treating coccidioides infection |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1544722A (fr) * | 1966-05-17 | 1968-11-08 | Whitefin Holding Sa | Dérivés du pyrrole et leur procédé de fabrication |
| GB1154745A (en) * | 1966-05-17 | 1969-06-11 | Whitefin Holding Sa | Haloketones |
-
0
- BE BE790747D patent/BE790747A/xx not_active IP Right Cessation
-
1972
- 1972-10-23 GB GB4878172A patent/GB1405148A/en not_active Expired
- 1972-10-24 US US00299726A patent/US3857857A/en not_active Expired - Lifetime
- 1972-10-25 IL IL40665A patent/IL40665A/xx unknown
- 1972-10-27 AR AR244847A patent/AR194281A1/es active
- 1972-10-27 NL NLAANVRAGE7214580,A patent/NL178073C/xx not_active IP Right Cessation
- 1972-10-27 YU YU02672/72A patent/YU267272A/xx unknown
- 1972-10-27 CA CA155,097A patent/CA974245A/en not_active Expired
- 1972-10-27 NO NO3880/72A patent/NO137784C/no unknown
- 1972-10-27 SE SE7213899A patent/SE387940B/xx unknown
- 1972-10-27 DK DK533472AA patent/DK138642B/da not_active IP Right Cessation
- 1972-10-30 FI FI3006/72A patent/FI54105C/fi active
- 1972-10-30 CH CH1582572A patent/CH583194A5/xx not_active IP Right Cessation
- 1972-10-30 FR FR7238462A patent/FR2158056B1/fr not_active Expired
- 1972-10-30 CS CS7290A patent/CS174859B2/cs unknown
- 1972-10-30 AU AU48321/72A patent/AU475877B2/en not_active Expired
- 1972-10-30 IE IE1460/72A patent/IE36907B1/xx unknown
- 1972-10-30 SU SU1848312A patent/SU533334A3/ru active
- 1972-10-30 DE DE2253150A patent/DE2253150C3/de not_active Expired
- 1972-10-30 JP JP10808572A patent/JPS5418247B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE790747A (fr) | 1973-02-15 |
| NL7214580A (enExample) | 1973-05-02 |
| CA974245A (en) | 1975-09-09 |
| JPS5418247B2 (enExample) | 1979-07-06 |
| NO137784B (no) | 1978-01-16 |
| FI54105C (fi) | 1978-10-10 |
| CH583194A5 (enExample) | 1976-12-31 |
| JPS4852764A (enExample) | 1973-07-24 |
| US3857857A (en) | 1974-12-31 |
| FR2158056B1 (enExample) | 1976-04-23 |
| SE387940B (sv) | 1976-09-20 |
| IE36907L (en) | 1973-04-30 |
| FR2158056A1 (enExample) | 1973-06-08 |
| DE2253150B2 (de) | 1981-03-19 |
| FI54105B (fi) | 1978-06-30 |
| NL178073B (nl) | 1985-08-16 |
| AU475877B2 (en) | 1976-09-09 |
| AU4832172A (en) | 1974-05-02 |
| NO137784C (no) | 1978-04-26 |
| DK138642C (enExample) | 1979-03-12 |
| AR194281A1 (es) | 1973-06-29 |
| YU267272A (en) | 1982-02-28 |
| DE2253150A1 (de) | 1973-05-10 |
| CS174859B2 (enExample) | 1977-04-29 |
| NL178073C (nl) | 1986-01-16 |
| IL40665A (en) | 1975-06-25 |
| GB1405148A (en) | 1975-09-03 |
| DE2253150C3 (de) | 1982-02-11 |
| DK138642B (da) | 1978-10-09 |
| IL40665A0 (en) | 1972-12-29 |
| IE36907B1 (en) | 1977-03-16 |
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