Dimethylformamide → (2S,4R)-2-(dimethylcarbamoyl)methyloxymethyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

To a mixture of dimethylformamide (3.9 ml) and tetrahydrofuran (30 ml) was dropwise added phosphorus oxychloride (3.75 ml) at 0°-10° C. and the mixture was stirred at the same temperature for 30 minutes. To the mixture was added a solution of (2S,4R)-2-(carboxymethyloxymethyl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (14.50 g) in tetrahydrofuran (15 ml) at 0°-10° C. and the mixture was stirred at the same temperature for 30 minutes. The resulting mixture was dropwise added to a mixture of dimethylamine hydrochloride (50 g) and triethylamine (100 ml) in methanol (200 ml) at 0°-10° C. with stirring. The mixture was stirred at the same temperature for 2 hours. The insoluble material was filtered off and the filtrate was concentrated under reduced pressure to give a syrup. The syrup was dissolved in ethyl acetate (200 ml), washed with water (200 ml), 1N hydrochloric acid (200 ml), saturated aqueous sodium hydrogen carbonate (200 ml) and brine (200 ml), in turn, dried over magnesium sulfate, and concentrated under reduced pressure to give (2S,4R)-2-(dimethylcarbamoyl)methyloxymethyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (12.03 g).

1. customat 0°-10° C.
2. stirringthe mixture was stirred at the same temperature for 30 minutes
3. stirringwith stirring
4. stirringThe mixture was stirred at the same temperature for 2 hours
5. filtrationThe insoluble material was filtered off
6. concentrationthe filtrate was concentrated under reduced pressure
7. customto give a syrup
8. washwashed with water (200 ml), 1N hydrochloric acid (200 ml), saturated aqueous sodium hydrogen carbonate (200 ml) and brine (200 ml), in turn
9. dry with materialdried over magnesium sulfate
10. concentrationconcentrated under reduced pressure

ORDレコード

ord-e3b3e852e32047a486dd1f0df75fbe4e

出典データセット

uspto-grants-1991_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04983596