Pyridine → HCID 11095182, compound

Temperature

-15 °C

To an oven-dried, septaed 10 mL round-bottom flask, cooled under an argon atmosphere, and charged with N-BOC-glycine, 24a, (175.2 mg, 1.00 mmol) was added 2.5 mL freshly distilled CH2Cl2 under argon. The reaction was cooled to −15° C. and to the flask was added cyanuric fluoride (450 μL, 5 mmol). The reaction was stirred at −15° C. for 15 minutes then anhydrous pyridine (81 μL, 1.0 mmol) was added. Stirring was maintained at −15° C. for 90 minutes, with reaction progress indicated by the gradual formation of a precipitate. Without warming, the crude reaction was poured over ice, and immediately extracted twice with CH2Cl2. The combined CH2Cl2 extracts were washed once with water, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The product crystallized upon storage at 0° C., affording 145.6 mg of 25a as white crystals. FTIR (neat) 1859 cm−1.

1. temperaturecooled under an argon atmosphere
2. stirringStirring
3. temperaturewas maintained at −15° C. for 90 minutes, with reaction progress
4. temperatureWithout warming
5. customthe crude reaction
6. additionwas poured over ice
7. extractionimmediately extracted twice with CH2Cl2
8. washThe combined CH2Cl2 extracts were washed once with water
9. dry with materialdried over anhydrous magnesium sulfate
10. filtrationfiltered
11. concentrationconcentrated in vacuo
12. customThe product crystallized upon storage at 0° C.

ORD record

ord-d99ec83fcff14e1aab62c09d9f7c552f

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07045360B2