GB595958A - Improvements in and relating to the manufacture of derivatives of thiazolidines and of cysteine - Google Patents
Improvements in and relating to the manufacture of derivatives of thiazolidines and of cysteineInfo
- Publication number
- GB595958A GB595958A GB1770645A GB1770645A GB595958A GB 595958 A GB595958 A GB 595958A GB 1770645 A GB1770645 A GB 1770645A GB 1770645 A GB1770645 A GB 1770645A GB 595958 A GB595958 A GB 595958A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethylene oxide
- lactone
- treated
- general formula
- boron trifluoride
- 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
- 150000003548 thiazolidines Chemical class 0.000 title abstract 3
- XUJNEKJLAYXESH-REOHCLBHSA-N L-cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 title 1
- 235000018417 cysteine Nutrition 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N Boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 abstract 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 5
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 4
- 150000002596 lactones Chemical class 0.000 abstract 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 4
- OWVZJBQLZUPHDC-UHFFFAOYSA-N 2-(1,3-thiazolidin-3-yl)ethanol Chemical class OCCN1CCSC1 OWVZJBQLZUPHDC-UHFFFAOYSA-N 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N Benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- 230000000875 corresponding Effects 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N Barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- LWJROJCJINYWOX-UHFFFAOYSA-L Mercury(II) chloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 229910001864 baryta Inorganic materials 0.000 abstract 1
- 229940095076 benzaldehyde Drugs 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- 150000001944 cysteine derivatives Chemical class 0.000 abstract 1
- 238000000354 decomposition reaction Methods 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 1
- -1 ethylene halohydrin Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 150000001261 hydroxy acids Chemical class 0.000 abstract 1
- 229960002523 mercuric chloride Drugs 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 125000001984 thiazolidinyl group Chemical group 0.000 abstract 1
- 238000010792 warming Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Thiazolidine derivatives of the general formula <FORM:0595958/IV/1> (wherein R1 and R2 represent alkyl radicals, R3 hydrogen or an alkyl or aryl radical, which may carry substituents and R4 hydrogen or an alkyl radical), or the corresponding lactones, are manufactured by treating a thiazolidine derivative of the general formula <FORM:0595958/IV/2> with ethylene oxide or an ethylene halohydrin. When ethylene oxide is used, the reaction is advantageously effected in the presence of a solvent and of boron trifluoride as condensing agent, whereby the lactone is formed at higher and the free hydroxy acid at lower temperatures, the former being convertible to the latter by shaking with cold baryta solution whilst the reverse charge is effected by mild dehydration, e.g. by the action of acetic anhydride. The products are converted into cysteine derivatives of the general formula <FORM:0595958/IV/3> by rupturing the thiazolidine ring by hydrolysis on heating with strong hydrochloric acid or a chloride of a metal which has an insoluble sulphide (e.g. with aqueous mercuric chloride followed by decomposition of the resultant complex with sulphuretted hydrogen). In examples: (1) isopropylidenepenicillamine (R1 = R2 = R3 = R4 = CH3) is heated in a sealed tube in suspension in chloroform containing ethylene oxide and a solution of boron trifluoride in ether, yielding the lactone; (2) the product of (1) is heated with hydrochloric acid to produce N-hydroxyethylpenicillamine hydrochloride; (3) 2 - phenyl - 4 : 4 - dimethyl - 5 - carboxythiazolidine (prepared from benzaldehyde and b : b -dimethylcysteine) is treated at 0 DEG C. with ethylene oxide in chloroform in the presence of ethereal boron trifluoride, yielding the corresponding N-hydroxyethylthiazolidine derivative; (4) the product of (3) is converted into its lactone by warming with acetic anhydride; (5) a - ethyl dihydropenicilloate - I <FORM:0595958/IV/4> is treated as in (3); (6) the product of (5) is treated as in (4). Specifications 584,918 and 585,413 are referred to.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB595958A true GB595958A (en) | 1947-12-23 |
Family
ID=1733339
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1770645A Expired GB595958A (en) | 1945-07-11 | Improvements in and relating to the manufacture of derivatives of thiazolidines and of cysteine |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB595958A (en) |
-
1945
- 1945-07-11 GB GB1770645A patent/GB595958A/en not_active Expired
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