Water → (2S)-1-((tert-butoxy)carbonyl)azetidine-2-carboxylic acid

(S)-(−)-2-Azetidinecarboxylic acid (Aldrich Chemical Company, Milwaukee, Wis.) (1.00 g, 9.89 mmol) is dissolved in 12 mL of 1:1 dioxane:water. Triethylamine (2.1 mL, 14.84 mmol) is added followed by BOC-ON (2.68 g, 10.9 mmol). The mixture is stirred for 6.75 hours then poured onto water (50 mL) and extracted with ether (7 times, 50 mL each). The aqueous solution is cooled in an ice-bath and the pH adjusted to approximately 2.5 with ice-cold 1N HCl solution. The resulting solution is extracted with methylene chloride (3 times, 50 mL each). The combined organic extracts are dried over MgSO4, filtered and concentrated in vacuo to afford an oil. Hexane (100 mL) is added to this oil and the mixture placed in the freezer overnight. The hexane is decanted and the product (1) dried under vacuum to afford a white solid. ISMS: MH+ 202.2

1. additionthen poured onto water (50 mL)
2. extractionextracted with ether (7 times, 50 mL each)
3. temperatureThe aqueous solution is cooled in an ice-bath
4. extractionThe resulting solution is extracted with methylene chloride (3 times, 50 mL each)
5. dry with materialThe combined organic extracts are dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customto afford an oil
9. customplaced in the freezer overnight
10. customThe hexane is decanted
11. dry with materialthe product (1) dried under vacuum
12. customto afford a white solid

ORD record

ord-11f4203ed25f4c79b57be055373534a3

Source dataset

uspto-grants-2006_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07018642B2