JPS5490190A - Preparation of optical isomer of alpha-amino-p-hydroxybenzylpenicillin - Google Patents
Preparation of optical isomer of alpha-amino-p-hydroxybenzylpenicillinInfo
- Publication number
- JPS5490190A JPS5490190A JP15550477A JP15550477A JPS5490190A JP S5490190 A JPS5490190 A JP S5490190A JP 15550477 A JP15550477 A JP 15550477A JP 15550477 A JP15550477 A JP 15550477A JP S5490190 A JPS5490190 A JP S5490190A
- Authority
- JP
- Japan
- Prior art keywords
- isomer
- compound
- optical isomer
- solvent
- residue
- 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
- 230000003287 optical effect Effects 0.000 title abstract 3
- LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical class [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 abstract 2
- 239000013078 crystal Substances 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 abstract 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001447 alkali salts Chemical class 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
Abstract
PURPOSE: To separate the D isomer of the titled substance having improved antibacterial activity from an aqueous layer with ease, by adding a specific solvent to an aqueous solution of the optical isomer mixture of the titled compound which is obtained by reducing the acylated 6-aminopenicillanic acid.
CONSTITUTION: 6-aminopenicillanic acid, preferably an alkali salt, is reacted with a compound of formula I: (X is halogen) in a solvent, and the reaction mixture is hydrogenated in the presence of Pd-active carbon to form an optical isomer mixture of the compound of formula II. The solvent is distilled away, and 1N hydrochlonic acid is added to adjust pH to 2.0 or below, preferably 0.9W1.0. The solution of the residue is incorporated with isobutyl methyl ketone in an amount of about 10W20 times that of the residue, and agitated thoroughly, to separate an aqueous layer. The pH of the layer is adjusted to preferably 5 to give crystals of the D isomer of the titled compound. The D isomer is filtered and concentrated to from crystals of the L isomer.
COPYRIGHT: (C)1979,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15550477A JPS5490190A (en) | 1977-12-26 | 1977-12-26 | Preparation of optical isomer of alpha-amino-p-hydroxybenzylpenicillin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15550477A JPS5490190A (en) | 1977-12-26 | 1977-12-26 | Preparation of optical isomer of alpha-amino-p-hydroxybenzylpenicillin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS5490190A true JPS5490190A (en) | 1979-07-17 |
Family
ID=15607481
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15550477A Pending JPS5490190A (en) | 1977-12-26 | 1977-12-26 | Preparation of optical isomer of alpha-amino-p-hydroxybenzylpenicillin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5490190A (en) |
-
1977
- 1977-12-26 JP JP15550477A patent/JPS5490190A/en active Pending
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