Reaktion #344459

Reaktionsgleichung

t-butyl (S)-2,2-dimethyl-4-(p-tolylsulfonyloxymethyl)-3-oxazolidinecaboxylate

sodium hydride

4-methyl-3H-1,4-benzodiazepine-2,5(1H, 4H)-dione

→

t-butyl (R)-(2,3,4,5-tetrahydro-4-methyl-2,5-dioxo-1H-1,4-benzodiazepin-1-ylmethyl)-2,2-dimethyl-3-oxazolidinecarboxylate

Ausbeute 33.3%

Lösungsmittel

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigedoes not exceed 35° C.
2. 2
   workup.STIRRINGthe mixture is stirred at 50° C. overnight
3. 3
   SonstigeThe reaction mixture is evaporated
4. 4
   Waschenwashed with water
5. 5
   Sonstigedried
6. 6
   SonstigeAfter evaporation of the solvent the residue
7. 7
   Sonstigeis purified over silica gel with ethyl acetate/hexane (1:1)

Vorschrift

1.1 g of sodium hydride dispersion (60%) are suspended in 50 ml of DMF. 5.23 g of 4-methyl-3H-1,4-benzodiazepine-2,5(1H, 4H)-dione are added thereto so that the temperature does not exceed 35° C. and the mixture is stirred at room temperature for 90 minutes. Subsequently, a solution of 5.3 g of t-butyl (S)-2,2-dimethyl-4-(p-tolylsulfonyloxymethyl)-3-oxazolidinecaboxylate (Example 6a) in 50 ml of DMF is added thereto and the mixture is stirred at 50° C. overnight. The reaction mixture is evaporated and the residue is taken up in ethyl acetate, washed with water and dried. After evaporation of the solvent the residue is purified over silica gel with ethyl acetate/hexane (1:1). There are obtained 1.85 g of t-butyl (R)-(2,3,4,5-tetrahydro-4-methyl-2,5-dioxo-1H-1,4-benzodiazepin-1-ylmethyl)-2,2-dimethyl-3-oxazolidinecarboxylate.

Quelle