JPS6456686A - Stereo-selective synthesis of beta-lactam compound - Google Patents
Stereo-selective synthesis of beta-lactam compoundInfo
- Publication number
- JPS6456686A JPS6456686A JP62213792A JP21379287A JPS6456686A JP S6456686 A JPS6456686 A JP S6456686A JP 62213792 A JP62213792 A JP 62213792A JP 21379287 A JP21379287 A JP 21379287A JP S6456686 A JPS6456686 A JP S6456686A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- reacting
- lithium
- beta
- compound
- 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
- -1 beta-lactam compound Chemical class 0.000 title abstract 4
- 230000015572 biosynthetic process Effects 0.000 title 1
- 230000000707 stereoselective effect Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 229910052744 lithium Inorganic materials 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 abstract 2
- INAHHIFQCVEWPW-RXMQYKEDSA-N (5r)-1-azabicyclo[3.2.0]heptan-7-one Chemical compound C1CCN2C(=O)C[C@H]21 INAHHIFQCVEWPW-RXMQYKEDSA-N 0.000 abstract 1
- WHBMMWSBFZVSSR-UHFFFAOYSA-N R3HBA Natural products CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 239000002243 precursor Substances 0.000 abstract 1
- 239000002994 raw material 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
- 125000004665 trialkylsilyl group Chemical group 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
PURPOSE:To obtain the titled compound useful as a synthetic precursor for carbapenam antibiotic substance having high optical purity, advantageously on an industrial scale, by reacting a specific lithium enolate compound with a specific propynal imine derivative. CONSTITUTION:The objective compound of formula II is produced by reacting a lithium enolate compound of formula I (R<1> is lower alkyl or aryl; R<2> is alkyl) with a propynal imine derivative of formula R<3>CidenticalC-CH=NR<3> (R<3> is trialkylsilyl). The starting raw material of formula I can be produced by reacting a beta-hydroxybutyric acid ester of formula II with a dialkylzinc of formula ZnR<2> and reacting the resultant alkylzinc alcoholate with lithium diisopropylamide and/or lithium hexamethylenedisilazane.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62213792A JPS6456686A (en) | 1987-08-27 | 1987-08-27 | Stereo-selective synthesis of beta-lactam compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62213792A JPS6456686A (en) | 1987-08-27 | 1987-08-27 | Stereo-selective synthesis of beta-lactam compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6456686A true JPS6456686A (en) | 1989-03-03 |
| JPH0349912B2 JPH0349912B2 (en) | 1991-07-31 |
Family
ID=16645128
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62213792A Granted JPS6456686A (en) | 1987-08-27 | 1987-08-27 | Stereo-selective synthesis of beta-lactam compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6456686A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4887428B2 (en) * | 2006-11-13 | 2012-02-29 | ヨウル チョン ケミカル カンパニー， リミテッド | Raw material quantitative supply apparatus and method |
-
1987
- 1987-08-27 JP JP62213792A patent/JPS6456686A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4887428B2 (en) * | 2006-11-13 | 2012-02-29 | ヨウル チョン ケミカル カンパニー， リミテッド | Raw material quantitative supply apparatus and method |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0349912B2 (en) | 1991-07-31 |
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