Benzyl Bromide → 4-(1-benzyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-5-yl)-piperazine-1-carboxylic acid tert-butyl ester

温度

0 °C

To a solution of 4-(2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-5-yl)-piperazine-1-carboxylic acid tert-butyl ester (43 mg, 0.13 mmol) in 2 ml anhydrous dimethylformamide was added sodium hydride (8 mg of a 60% suspension in mineral oil, 0.2 mmol) portion-wise at 0° C. The solution was stirred with a magnetic stirrer at 0° C. for 20 minutes, at which time the initial off-gassing ended. Benzyl bromide (0.02 ml, 0.17 mmol) was added in one portion and the reaction mixture was stirred at 0° C. for an hour. The solution was allowed to warm to room temperature and the reaction mixture was partitioned between water and ethyl acetate. The aqueous layer was extracted with ethyl acetate and the combined organic fractions were washed with water and brine. After drying over MgSO4, the organic fraction was concentrated in vacuo and resulting brown residue was purified by prep TLC to give 33 mg of 4-(1-benzyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-5-yl)-piperazine-1-carboxylic acid tert-butyl ester as a white solid (60%). MS: 424 (M+H)+.

1. stirringthe reaction mixture was stirred at 0° C. for an hour
2. temperatureto warm to room temperature
3. customthe reaction mixture was partitioned between water and ethyl acetate
4. extractionThe aqueous layer was extracted with ethyl acetate
5. washthe combined organic fractions were washed with water and brine
6. dry with materialAfter drying over MgSO4
7. concentrationthe organic fraction was concentrated in vacuo
8. customresulting brown residue
9. customwas purified by prep TLC

ORDレコード

ord-c24a8583a31d4196b1ffd1c4da84feeb

出典データセット

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07365063B2