Hydroxylamine → HCID 86754433, Verbindung
Reaktionsgleichung
O=C[C@@H]([C@H]([C@@H]([C@@H]([CH2:11][OH:12])O)O)O)O.OP([O-])(O)=O.[K+].OP([O-])([O-])=O.[K+].[K+].[Cl-].[K+].[C:28]([CH:33]1[CH2:42][CH2:41][C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:34]1=[O:43])([O:30]CC)=[O:29].[NH2:44][OH:45]>>[C:28]([C:33]1([C:11]([NH:44][OH:45])=[O:12])[CH2:42][CH2:41][C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:34]1=[O:43])([OH:30])=[O:29]Komponenten
Edukt 6
Produkt 1
Versuchsvorschrift
Rhizopus arrhizus (ATCC 11145) is cultured according to the method of Buisson and Azerad (Tet. Lett. 27, 2631-2634 (1986), herein incorporated by reference) in one liter of a medium of glucose (30 grams), KH2PO4 (1 gram), K2HPO4 (2 grams), corn steep-liquor (10 grams) MgSO4.7H2O (0.5 gram), NaNO3 (2 grams), FeSO4.7H2O (0.02 gram), and KCl (0.5 gram) with rotary shaking at 25° C. Two grams of 2-carboxy-1-tetralone hydroxamic acid, produced by the reaction of 2-carboethoxy-1-tetralone with hydroxylamine, is dissolved in 2 ml of 95% ethanol, the resulting solution is added to the culture, and shaking is resumed. The reaction is followed by TLC (staining with anisaldehyde) to monitor the consumption of starting material and the production of product alcohol. After 48-72 hours the reaction is judged complete, and the reaction is terminated by removing from the shaker and adding 20-30 grams of Celite. The resulting suspension is suction filtered through a pad of Celite and the dear yellow filtrate is extracted with ethyl acetate (4×200 ml). The extracts are combined, dried over MgSO4, filtered, and rotary evaporated to leave 1 gram of a yellowish solid containing as the major product (1S,2R)-1-hydroxy-2-carboxytetralin hydroxamic acid.
Quellen und Nachweise
- ORD-Eintrag
- ord-701549435f164106a18568d845b86f5f
- Quelldatensatz
- uspto-grants-1999_08
- Patentnummer
- US05942644
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