Hydrochloric Acid → HCID 13578774, compound

Temperature

-20 °C

A mixture of 17.5 g of N-BOC glycine, 100 ml of methylene chloride and 13.7 ml of N-methyl-morpholine was cooled to -20° C. and a solution of 13 ml of isobutyl chloroformate in 50 ml of methylene chloride was added. After stirring for 30 minutes at -20° C., a solution of 10.25 g of 2-amino-3-trifluoromethyl benzoic acid [prepared by the process of J. Med. Chem., Vol. 16 (2) 101,6 (1973)] in 5.49 ml of N-methyl-morpholine and 120 ml of methylene chloride was added thereto and after stirring for 20 hours at ambient temperature, the mixuture was poured into 500 ml of water and 150 ml of 2N hydrochloric acid. The mixture was extracted with methylene chloride and the organic phase was washed with water, dried and concentrated under reduced pressure to dryness. The residue was triturated with 50 ml of methanol and the mixture was frozen, separated, washed with methanol and dried under reduced pressure at 50° C. to obtain 11 g of 1,1-dimethylethyl [(4-oxo-8-(trifluoromethyl)-4H-3,1-benzoxazin-2-yl)-methyl]-carbamate melting at 176° C.

1. stirringafter stirring for 20 hours at ambient temperature
2. extractionThe mixture was extracted with methylene chloride
3. washthe organic phase was washed with water
4. customdried
5. concentrationconcentrated under reduced pressure to dryness
6. customThe residue was triturated with 50 ml of methanol
7. temperaturethe mixture was frozen
8. customseparated
9. washwashed with methanol
10. customdried under reduced pressure at 50° C.

ORD record

ord-d81250954ba64849961ef6706f2663e5

Source dataset

uspto-grants-1987_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04636512