Triethylamine → HCID 23003636, compound

Temperature

0 °C

To a solution of 5-methylisoxazole-4-carboxylic acid (500 mg, 3.94 mmol) in a mixture of acetone (10 mL) and water (3 mL) was added triethylamine (0.83 mL, 5.91 mmol). The mixture was cooled to 0° C. in a ice-bath. Ethylchloroformate (640 mg, 5.91 mmol) was then added and the resulting mixture was stirred for 1.5 hours at 0° C. To the mixture was added sodium azide (410 mg, 6.30 mmol), and the mixture was stirred for another 2 hours. The mixture was concentrated, the residue was diluted with dichloromethane and washed with water. The organic layer was dried over MgSO4 and concentrated to give crude material, which was carried on to the coupling without further purification.

1. stirringthe mixture was stirred for another 2 hours
2. concentrationThe mixture was concentrated
3. additionthe residue was diluted with dichloromethane
4. washwashed with water
5. dry with materialThe organic layer was dried over MgSO4
6. concentrationconcentrated
7. customto give crude material, which
8. customwas carried on to the coupling without further purification

ORD record

ord-09b818ffde474886af0e383300379822

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06608077B2