GB1395458A - Process for the preparation of the optical antipodes of pantolactone - Google Patents
Process for the preparation of the optical antipodes of pantolactoneInfo
- Publication number
- GB1395458A GB1395458A GB5016973A GB5016973A GB1395458A GB 1395458 A GB1395458 A GB 1395458A GB 5016973 A GB5016973 A GB 5016973A GB 5016973 A GB5016973 A GB 5016973A GB 1395458 A GB1395458 A GB 1395458A
- Authority
- GB
- United Kingdom
- Prior art keywords
- lithium
- pantoate
- pantolactone
- polar solvent
- optically
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/01—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups
- C07C59/10—Polyhydroxy carboxylic acids
Abstract
1395458 Optical resolution of D,L-pantolactone JENAPHARM VEB 29 Oct 1973 [4 June 1973] 50169/73 Heading C2C The optical resolution of D,L-pantolactone is effected by converting the latter into D,L- lithium pantoate, resolving this racemic salt by selective crystallization from a polar solvent (e.g. CH 3 OH, C 2 H 5 OH) or by electrostatic separation of the racemic mixture crystallized from a polar solvent and subsequently converting the optically-active forms of lithium pantoate thus produced into optically-active pantolactone. The undesired optically-active form of lithium pantoate obtained as a by-product is preferably dissolved or suspended in a polar solvent (e.g. H 2 O, CH 3 OH, C 2 H 5 OH) and racemized at an elevated temperature (e.g. 120-180 C.) and optionally in the presence of a basic catalyst (e.g. an aliphatic amine or an alkali metal hydroxide or carbonate). The D,L-lithium pantoate is obtained by reacting D,L-pantolactone with a basic lithium compound (e.g. LiOH, Li 2 CO 3 ) in a polar solvent or by the double decomposition of an appropriate pair of salts (e.g. calcium pantoate/lithium oxalate, barium pantoate/lithium sulphate) in an aqueous medium.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN490/CAL/74A IN137547B (en) | 1973-10-29 | 1974-03-07 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD171272A DD109380A1 (en) | 1973-06-04 | 1973-06-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1395458A true GB1395458A (en) | 1975-05-29 |
Family
ID=5491480
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5016973A Expired GB1395458A (en) | 1973-06-04 | 1973-10-29 | Process for the preparation of the optical antipodes of pantolactone |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS5512433B2 (en) |
| AR (1) | AR201439A1 (en) |
| AT (1) | AT339511B (en) |
| BE (1) | BE828391Q (en) |
| CH (2) | CH603613A5 (en) |
| CS (1) | CS179302B1 (en) |
| DD (1) | DD109380A1 (en) |
| DE (1) | DE2350610C3 (en) |
| FR (1) | FR2231638B1 (en) |
| GB (1) | GB1395458A (en) |
| IE (1) | IE38777B1 (en) |
| IS (1) | IS949B6 (en) |
| IT (1) | IT1035078B (en) |
| NL (1) | NL7407401A (en) |
| RO (2) | RO63651A (en) |
| SE (1) | SE417511B (en) |
| SU (1) | SU577997A3 (en) |
| YU (1) | YU36945B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4167522A (en) * | 1977-09-05 | 1979-09-11 | A.E.C. Societe De Chimie Organique Et Biologique | Guanidine pantoate |
| CN111499602A (en) * | 2020-05-14 | 2020-08-07 | 吴江 | Method for extracting D-pantolactone from D L-pantolactone split liquid by calcium salt method |
| CN112047906A (en) * | 2019-06-07 | 2020-12-08 | 帝斯曼知识产权资产管理有限公司 | Racemization method of pantoyl lactone |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1522111A (en) * | 1966-05-10 | 1968-04-19 | Fuji Chemical Ind | Process for resolving racemic ammonium pantoate |
| JPS5021448B1 (en) * | 1966-05-10 | 1975-07-23 |
-
1973
- 1973-06-04 DD DD171272A patent/DD109380A1/xx unknown
- 1973-10-09 DE DE2350610A patent/DE2350610C3/en not_active Expired
- 1973-10-29 GB GB5016973A patent/GB1395458A/en not_active Expired
-
1974
- 1974-01-14 JP JP745374A patent/JPS5512433B2/ja not_active Expired
- 1974-01-22 IE IE126/74A patent/IE38777B1/en unknown
- 1974-05-17 IT IT51089/74A patent/IT1035078B/en active
- 1974-05-24 AR AR253919A patent/AR201439A1/en active
- 1974-05-27 AT AT435974A patent/AT339511B/en not_active IP Right Cessation
- 1974-05-31 IS IS2215A patent/IS949B6/en unknown
- 1974-05-31 NL NL7407401A patent/NL7407401A/xx not_active Application Discontinuation
- 1974-05-31 SE SE7407275A patent/SE417511B/en unknown
- 1974-05-31 CS CS7400003903A patent/CS179302B1/en unknown
- 1974-05-31 FR FR7419015A patent/FR2231638B1/fr not_active Expired
- 1974-06-03 RO RO7400079036A patent/RO63651A/en unknown
- 1974-06-03 SU SU7402031936A patent/SU577997A3/en active
- 1974-06-03 YU YU1528/74A patent/YU36945B/en unknown
- 1974-06-03 RO RO7487342A patent/RO69917A/en unknown
- 1974-06-04 CH CH1318077A patent/CH603613A5/xx not_active IP Right Cessation
- 1974-06-04 CH CH758674A patent/CH602691A5/xx not_active IP Right Cessation
-
1975
- 1975-04-25 BE BE155773A patent/BE828391Q/en not_active IP Right Cessation
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4167522A (en) * | 1977-09-05 | 1979-09-11 | A.E.C. Societe De Chimie Organique Et Biologique | Guanidine pantoate |
| CN112047906A (en) * | 2019-06-07 | 2020-12-08 | 帝斯曼知识产权资产管理有限公司 | Racemization method of pantoyl lactone |
| CN111499602A (en) * | 2020-05-14 | 2020-08-07 | 吴江 | Method for extracting D-pantolactone from D L-pantolactone split liquid by calcium salt method |
| CN111499602B (en) * | 2020-05-14 | 2022-06-07 | 安徽泰格生物科技有限公司 | Method for extracting D-pantolactone from DL-pantolactone split liquid by calcium salt method |
Also Published As
| Publication number | Publication date |
|---|---|
| AU6942374A (en) | 1975-11-27 |
| IS949B6 (en) | 1976-10-04 |
| JPS5052052A (en) | 1975-05-09 |
| FR2231638A1 (en) | 1974-12-27 |
| SE417511B (en) | 1981-03-23 |
| NL7407401A (en) | 1974-12-06 |
| YU36945B (en) | 1984-08-31 |
| FR2231638B1 (en) | 1976-06-25 |
| RO69917A (en) | 1981-06-21 |
| DD109380A1 (en) | 1974-11-05 |
| DE2350610B2 (en) | 1975-05-22 |
| CH603613A5 (en) | 1978-08-31 |
| CH602691A5 (en) | 1978-07-31 |
| CS179302B1 (en) | 1977-10-31 |
| YU152874A (en) | 1982-06-18 |
| AR201439A1 (en) | 1975-03-14 |
| IE38777B1 (en) | 1978-05-24 |
| IS2215A7 (en) | 1974-12-05 |
| RO63651A (en) | 1978-09-15 |
| BE828391Q (en) | 1975-08-18 |
| AT339511B (en) | 1977-10-25 |
| DE2350610A1 (en) | 1974-12-19 |
| ATA435974A (en) | 1977-02-15 |
| IT1035078B (en) | 1979-10-20 |
| SE7407275L (en) | 1974-12-05 |
| DE2350610C3 (en) | 1976-01-02 |
| IE38777L (en) | 1974-12-04 |
| JPS5512433B2 (en) | 1980-04-02 |
| SU577997A3 (en) | 1977-10-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |