* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
A mixture of (S)-2-azetidinecarboxyic acid (1Og, 98.9mmol), di-tert butyl dicarbonate (28.06g, 128.6mmol), N-methyl morpholine (11.5g, 113.7mmol), 1,4-dioxane (160ml) and water (160ml) was stirred at O0C for 4 hours and then at ambient temperature for 18 hours. The volatiles were removed by evaporation and the residue was dissolved in water, washed with DCM and the aqueous layer acidified to pH 1.0 at O0C with concentrated hydrochloric acid. The aqueous layer was extracted with DCM and the organic layer dried (Na2SO4) over anhydrous sodium sulfate to give iV-tert-butyloxycarbonylazetidin-2-yl carboxylic acid (12.61g, 63.1%) as an oil; NMR Spectrum (CDCl3) 1.42 (s, 9H), 2.40 (m, IH), 2.59 (m, IH), 3.90 (m, 2H), 4.80 (t, IH).
With 4-methyl-morpholine; In 1,4-dioxane; water;
41 a. 1-(t-butyloxycarbonyl)-azetidine-2-carboxylic acid A 10.15 g (100.39 mmol) sample of (S)-azetidine-2-carboxylic acid (Fluka) was dissolved in 300 mL of 1:1 H2 O: dioxane and stirred under N2. To this solution was added 12.64 mL (115 mmol) of N-methylmorpholine (NMM), and the solution was cooled to to 0 C. To the cooled solution was slowly added 29.98 mL (130 mmol) of di-t-butyl dicarbonate, and the reaction mixture was allowed to warm to room temperature and stirred for 16 hr. An additional 10 mg of di-t-butyl dicarbonate was added and the reaction was stirred for 2 hours longer. The reaction was quenched by pouring it into 250 mL of satd aqueous Na2 CO3, and the mixture was washed with ethyl acetate. The aqueous solution was adjusted to pH 2 with 10% citric acid and 3M HCl and extracted with ethyl acetate. The extracts were dried over Na2 SO4 and the solvent was removed under vacuum to give the title product as a white solid. MS: 21 9 (m, 2(M+NH4)+, (M+H)+. 1 H NMR (CDCl3) delta: 1.48 (s, 9H), 2.4-2.6 (b, 2H), 3.88=3.98 (m, 2H), 4.80 (b, 1H).
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
120K+ Compounds
Competitive Price
1-2 Day Shipping
