Diethyl Ether → (S,S)-Azepane-1-carboxylic acid {1-[2-(4-benzyloxy-phenyl)-1-diethylaminomethyl-ethylcarbamoyl]-3-methyl-butyl}-amide

온도

25 °C

A solution of 53 mg (0.20 mmol) of (S)-2-[(azepane-1-carbonyl)-amino]-4-methyl-pentanoic acid (Example 1, Step B) and 0.079 mL (7.2 mmol) 4-methylmorpholine in 4 mL DMF was stirred at 25° C. for 0.5 hour, and 82 mg (0.21 mmol) 0-benzotriazol-1-yl-N,N,N′,N′-bis(tetramethylene)uronium hexafluorophosphate was added. The resulting solution was cooled in an ice-bath and stirred 30 minutes, after which 64 mg (0.20 mmol) of (S)-3-(4-benzyloxy-phenyl)-N1,N1-diethyl-propane-1,2-diamine in 2 mL DMF was added. The resulting solution was warmed to 25° C. and stirred for 30 minutes. The mixture was then poured into 30 mL diethyl ether, and washed with 25 mL each of 5% HCl solution, brine, saturated aqueous sodium bicarbonate solution, and finally twice with brine. The mixture was dried over anhydrous sodium sulfate and concentrated at reduced pressure to give a clear, colorless oil that was purified by preparative thin-layer chromatography on a 500 μm silica gel plate using 50:50:1 ethyl acetate:hexane:methanol as eluant to give 21.2 mg (19%) of the title compound as a clear, colorless oil.

1. temperatureThe resulting solution was cooled in an ice-bath
2. stirringstirred for 30 minutes
3. washwashed with 25 mL each of 5% HCl solution, brine, saturated aqueous sodium bicarbonate solution
4. dry with materialThe mixture was dried over anhydrous sodium sulfate
5. concentrationconcentrated at reduced pressure
6. customto give a clear, colorless oil that
7. customwas purified by preparative thin-layer chromatography on a 500 μm silica gel plate

ORD 기록

ord-df1de5fc082b4be487c096f45bc0890c

출처 데이터셋

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US06362174B1