Sodium Azide → (N,N-Dimethylcarbamoyl)methyl (2R)-4-[(3-azidopropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoate

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Reaction Steps

Following the general procedure for the preparation of azides of Description 16, (N,N-dimethylcarbamoyl)methyl (2R)-4-[(3-chloropropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoate (36c) (200 mg, 0.43 mmol) dissolved in 3 mL of anhydrous dimethyl sulfoxide (DMSO) was reacted with 130 mg (2.0 mmol) of sodium azide (NaN3). After work-up, the crude material (36d) 184 mg (91% yield) was obtained as a colorless viscous oil that was used in the next step without further purification. MS (ESI) m/z 471.2 (M+H)+, 493.1 (M+Na)+.

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