Reaktionsgleichung
Cl[CH2:2][C:3]([C:5]1[CH:13]=[CH:12][C:11]2[N:10]3[C:14](=[O:22])[O:15][C@@H:16]([CH2:17][NH:18][C:19](=[O:21])[CH3:20])[C@@H:9]3[CH2:8][C:7]=2[CH:6]=1)=[O:4].[N-:23]=[N+:24]=[N-:25].[Na+].CC(C)=O>O1CCCC1.C(Cl)Cl.CO.CO.C(OCC)(=O)C>[N:23]([CH2:2][C:3]([C:5]1[CH:13]=[CH:12][C:11]2[N:10]3[C:14](=[O:22])[O:15][C@@H:16]([CH2:17][NH:18][C:19](=[O:21])[CH3:20])[C@@H:9]3[CH2:8][C:7]=2[CH:6]=1)=[O:4])=[N+:24]=[N-:25]Komponenten
7
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Versuchsvorschrift
A mixture of (1S,9aS) N-[(7-chloroacetyl-9,9a-dihydro-3-oxo-1H,3H-oxazolo[3,4-a]indol-1-yl)methyl]acetamide (EXAMPLE 48, 43 mg) and sodium azide (82 mg) are stirred in aqueous tetrahydrofuran (66%) for 3 days. Acetone (1 ml) is added and the mixture was heated in an oil bath (38°-50°) for 8 hours then concentrated to an aqueous layer and extracted with ethylacetate (6×2 ml). The combined organic layers are dried over magnesium sulfate and concentrated to provide the product as as an oil. The oil is taken up in methylene chloride/methanol and then placed on a 100 μsilica preprative plate and developed in methanol/ethylacetate (10/90, 2×) to give the title compound. ##STR2##
Aufarbeitung
- temperaturethe mixture was heated in an oil bath (38°-50°) for 8 hours
- concentrationthen concentrated to an aqueous layer
- extractionextracted with ethylacetate (6×2 ml)
- dry with materialThe combined organic layers are dried over magnesium sulfate
- concentrationconcentrated
- customto provide the product as as an oil
Quellen und Nachweise
- ORD-Eintrag
- ord-344b5d26f989476db51adec38886cea4
- Quelldatensatz
- uspto-grants-1993_09
- Patentnummer
- US05247090
Verknüpfte Notizen
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