Réaction #6333

Équation de réaction

(1S,9aS) N-[(7-chloroacetyl-9,9a-dihydro-3-oxo-1H,3H-oxazolo[3,4-a]indol-1-yl)methyl]acetamide

(1S,9aS) N-[(7-Chloroacetyl-9,9a-dihydro-3-oxo-1H,3H-oxazolo[3,4-a]indol-1-yl)methyl]acetamide

sodium azide

Acetone

→

title compound

(1S,9aS) N-[(7-Azidoacetyl-9,9a-dihydro-3-oxo-1H,3H-oxazolo [3,4-a]indol-1-yl)methyl]acetamide

Solvants

tetrahydrofuran

methanol ethylacetate

methanol ethyl acetate

methylene chloride methanol

Conditions de réaction

Traitement

1. 1
   Températurethe mixture was heated in an oil bath (38°-50°) for 8 hours
2. 2
   Concentrationthen concentrated to an aqueous layer
3. 3
   Extractionextracted with ethylacetate (6×2 ml)
4. 4
   SéchageThe combined organic layers are dried over magnesium sulfate
5. 5
   Concentrationconcentrated
6. 6
   Autreto provide the product as as an oil

Mode opératoire

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##

Source