JPS5555193A - Novel preparation of penicillanic acid derivative - Google Patents
Novel preparation of penicillanic acid derivativeInfo
- Publication number
- JPS5555193A JPS5555193A JP12742278A JP12742278A JPS5555193A JP S5555193 A JPS5555193 A JP S5555193A JP 12742278 A JP12742278 A JP 12742278A JP 12742278 A JP12742278 A JP 12742278A JP S5555193 A JPS5555193 A JP S5555193A
- Authority
- JP
- Japan
- Prior art keywords
- penicillanic acid
- compound
- hydroxyphenylacetamido
- formula
- azido
- 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.)
- Pending
Links
- RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical class OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 title abstract 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 2
- 150000001299 aldehydes Chemical class 0.000 abstract 2
- 239000006227 byproduct Substances 0.000 abstract 2
- 150000002903 organophosphorus compounds Chemical class 0.000 abstract 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 239000008280 blood Substances 0.000 abstract 1
- 210000004369 blood Anatomy 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- GNFABDZKXNKQKN-UHFFFAOYSA-N tris(prop-2-enyl)phosphane Chemical compound C=CCP(CC=C)CC=C GNFABDZKXNKQKN-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Abstract
PURPOSE: To prepare the title compound easily, in high efficiency, by treating 6-(α- azido-p-hydroxyphenylacetamido)penicillanic acid with a specific organo-phosphorus compound, and after romoving the objective product from the reaction products, treating the by-products with an aldehyde.
CONSTITUTION: 6-(α-Azido-p-hydroxyphenylacetamido)penicillanic acid is reacted with an organo-phosphorus compound of formula P(R1)3(R1 is allyl or alkoxy), e.g. triallyl phosphine, in a mixture of water and a hydrophilic solvent such as acetonitrile, whereby the reduction and the optical resolution are carried out at the same time to afford the (-) compound of the formula. The (+) compound which is obtained as a by-product, is treated with an aldehyde R2-CHO (R2 is allyl or heterocyclic group), e.g. salicylaldehyde to give 6-[(-)α-amino-p-hydroxyphenylacetamido]penicillanic acid of the formula.
USE: An antibiotic agent which keeps high concentration in blood.
COPYRIGHT: (C)1980,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12742278A JPS5555193A (en) | 1978-10-18 | 1978-10-18 | Novel preparation of penicillanic acid derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12742278A JPS5555193A (en) | 1978-10-18 | 1978-10-18 | Novel preparation of penicillanic acid derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS5555193A true JPS5555193A (en) | 1980-04-22 |
Family
ID=14959561
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12742278A Pending JPS5555193A (en) | 1978-10-18 | 1978-10-18 | Novel preparation of penicillanic acid derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5555193A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5852291A (en) * | 1981-09-22 | 1983-03-28 | Kureha Chem Ind Co Ltd | Penicillin antibiotic derivative and its medicinal preparation |
-
1978
- 1978-10-18 JP JP12742278A patent/JPS5555193A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5852291A (en) * | 1981-09-22 | 1983-03-28 | Kureha Chem Ind Co Ltd | Penicillin antibiotic derivative and its medicinal preparation |
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