GB1276413A - Process for hydrolyzing desacetyl 7-aminocephalosporanic acid lactone - Google Patents
Process for hydrolyzing desacetyl 7-aminocephalosporanic acid lactoneInfo
- Publication number
- GB1276413A GB1276413A GB54155/70A GB5415570A GB1276413A GB 1276413 A GB1276413 A GB 1276413A GB 54155/70 A GB54155/70 A GB 54155/70A GB 5415570 A GB5415570 A GB 5415570A GB 1276413 A GB1276413 A GB 1276413A
- Authority
- GB
- United Kingdom
- Prior art keywords
- desacetyl
- lactone
- aminocephalosporanic acid
- reaction
- preferred
- 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
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/02—Preparation
- C07D501/04—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Abstract
1276413 Hydrolysis of 7-aminocephalosporanic acid lactone SMITH KLINE & FRENCH LABORATORIES 13 Nov 1970 [17 Nov 1969] 54155/70 Heading C2A A process for hydrolysing desacetyl 7-aminocephalosporanic acid lactone II to desacetyl cephalosporanic acid I comprises subjecting the lactone II in a basic water-containing medium to a pH of 11-13 for 5 seconds to 5 minutes. The pH and time of reaction are critical, as the labile #-lactam ring is easily hydrolysed, as well as the lactone ring, and secondary decomposition occurs above pH 13. A preferred temperature range for the reaction is 20-30 C., a preferred pH range is 11À5 to 12À5 and a preferred time of reaction is 5 to 60 seconds. The yields of desacetyl 7- aminocephalosporanic acid range from 8-30%, measured by standard bioassay methods. Thin layer or column chromatography on cellulose may be used to separate the products.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87748169A | 1969-11-17 | 1969-11-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1276413A true GB1276413A (en) | 1972-06-01 |
Family
ID=25370056
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB54155/70A Expired GB1276413A (en) | 1969-11-17 | 1970-11-13 | Process for hydrolyzing desacetyl 7-aminocephalosporanic acid lactone |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3607869A (en) |
| JP (1) | JPS4932550B1 (en) |
| BE (1) | BE757176A (en) |
| CA (1) | CA918656A (en) |
| CH (1) | CH534181A (en) |
| DE (1) | DE2055336A1 (en) |
| FR (1) | FR2067328B1 (en) |
| GB (1) | GB1276413A (en) |
| LU (1) | LU62058A1 (en) |
| NL (1) | NL7015871A (en) |
| ZA (1) | ZA706510B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3864338A (en) * | 1970-08-11 | 1975-02-04 | Squibb & Sons Inc | Process for the preparation of {66 {hu 2{b -cephalosporin aldehydes |
-
0
- BE BE757176D patent/BE757176A/en unknown
-
1969
- 1969-11-17 US US877481A patent/US3607869A/en not_active Expired - Lifetime
-
1970
- 1970-09-23 ZA ZA706510A patent/ZA706510B/en unknown
- 1970-10-10 JP JP45089234A patent/JPS4932550B1/ja active Pending
- 1970-10-13 CA CA095364A patent/CA918656A/en not_active Expired
- 1970-10-29 NL NL7015871A patent/NL7015871A/xx unknown
- 1970-10-29 FR FR707039082A patent/FR2067328B1/fr not_active Expired
- 1970-11-10 DE DE19702055336 patent/DE2055336A1/en active Pending
- 1970-11-13 LU LU62058D patent/LU62058A1/xx unknown
- 1970-11-13 GB GB54155/70A patent/GB1276413A/en not_active Expired
- 1970-11-17 CH CH1698270A patent/CH534181A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2055336A1 (en) | 1971-05-27 |
| ZA706510B (en) | 1971-05-27 |
| FR2067328A1 (en) | 1971-08-20 |
| LU62058A1 (en) | 1971-05-11 |
| US3607869A (en) | 1971-09-21 |
| NL7015871A (en) | 1971-05-19 |
| BE757176A (en) | 1971-04-07 |
| JPS4932550B1 (en) | 1974-08-31 |
| CA918656A (en) | 1973-01-09 |
| CH534181A (en) | 1973-02-28 |
| FR2067328B1 (en) | 1973-02-02 |
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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 |