GB2001985A - Penam and cephem production - Google Patents
Penam and cephem productionInfo
- Publication number
- GB2001985A GB2001985A GB7832264A GB7832264A GB2001985A GB 2001985 A GB2001985 A GB 2001985A GB 7832264 A GB7832264 A GB 7832264A GB 7832264 A GB7832264 A GB 7832264A GB 2001985 A GB2001985 A GB 2001985A
- Authority
- GB
- United Kingdom
- Prior art keywords
- silylating agent
- derivatives
- carrying
- carried out
- tertiary base
- 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.)
- Granted
Links
- 150000001782 cephems Chemical class 0.000 title 1
- WSHJJCPTKWSMRR-RXMQYKEDSA-N penam Chemical compound S1CCN2C(=O)C[C@H]21 WSHJJCPTKWSMRR-RXMQYKEDSA-N 0.000 title 1
- 239000003795 chemical substances by application Substances 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 2
- 150000001408 amides Chemical class 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- ZGUNAGUHMKGQNY-UHFFFAOYSA-N alpha-phenylglycine Chemical class OC(=O)C(N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 abstract 1
- 238000006884 silylation reaction Methods 0.000 abstract 1
- SIOVKLKJSOKLIF-HJWRWDBZSA-N trimethylsilyl (1z)-n-trimethylsilylethanimidate Chemical compound C[Si](C)(C)OC(/C)=N\[Si](C)(C)C SIOVKLKJSOKLIF-HJWRWDBZSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Abstract
A process for the preparation of derivatives of certain penicillanic and cephalosporanic acids is disclosed. Such derivatives have previously been prepared by reacting the relevant acid with a silylating agent, which product is then reacted with a suitably substituted alpha -amino- phenylacetic acid or a reactive derivative thereof. Any silyl groups are thereafter removed by hydrolysis. Such known reaction was carried out at elevated temperature in the presence of a tertiary base as a proton acceptor. The present invention improves such process, which is carried out at room temperature and in the absence of a tertiary base by either utilising an amide carrying one or more alkylsilyl substituents, e.g. N,O-bis(trimethylsilyl) acetamide, as silylating agent, or carrying out the silylation reaction, using a known silylating agent, in the presence of a substituted amide, e.g. dimethylacetamide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7832264A GB2001985B (en) | 1977-08-05 | 1978-08-04 | Process for the preparation of penicillanic and cephalosporanic acid derivatives |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3287277 | 1977-08-05 | ||
| GB7832264A GB2001985B (en) | 1977-08-05 | 1978-08-04 | Process for the preparation of penicillanic and cephalosporanic acid derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2001985A true GB2001985A (en) | 1979-02-14 |
| GB2001985B GB2001985B (en) | 1982-07-07 |
Family
ID=26261606
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7832264A Expired GB2001985B (en) | 1977-08-05 | 1978-08-04 | Process for the preparation of penicillanic and cephalosporanic acid derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2001985B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4278600A (en) | 1979-03-19 | 1981-07-14 | Bristol-Myers Company | Production of penicillins |
| GB2240102A (en) * | 1990-01-22 | 1991-07-24 | Biochemie Gmbh | Beta-lactam production |
| US5998610A (en) * | 1994-11-21 | 1999-12-07 | Biochemie Gesellschaft M.B.H. | Silylation process |
-
1978
- 1978-08-04 GB GB7832264A patent/GB2001985B/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4278600A (en) | 1979-03-19 | 1981-07-14 | Bristol-Myers Company | Production of penicillins |
| GB2240102A (en) * | 1990-01-22 | 1991-07-24 | Biochemie Gmbh | Beta-lactam production |
| EP0439096A3 (en) * | 1990-01-22 | 1992-06-10 | Biochemie Gesellschaft M.B.H. | Improvements in or relating to beta lactam production |
| GB2240102B (en) * | 1990-01-22 | 1993-10-20 | Biochemie Gmbh | Improvements in or relating to beta lactam production |
| US5998610A (en) * | 1994-11-21 | 1999-12-07 | Biochemie Gesellschaft M.B.H. | Silylation process |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2001985B (en) | 1982-07-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |