반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:25]([OH:27])=O)[CH2:10][C:11]1[CH:16]=[CH:15][C:14](OCC2C=CC=CC=2)=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[C:61]([NH2:65])([CH3:64])([CH3:63])[CH3:62]>CN(C=O)C.CCOCC>[CH3:4][C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:25]([NH:65][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:27])([CH3:2])[CH3:3]참가 물질
반응물 4
생성물 1
시약·촉매·용매 2
반응 조건
- 온도
- 0 °C
실험 절차
A solution of N-(tert-Butyloxycarbonyl)-O-benzyl-L-tyrosine (Bachem, 2.00 g, 5.38 mmol) in 20 mL of DMF was cooled to 0° C. and treated with i-Pr2NEt (1.5 mL, Aldrich, Milwaukee, Wis.) followed by O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluoro-phosphate (2.04 g, 5.38 mmol, Novabiochem, La Jolla, Calif.). The resulting suspension was stirred for 30 minutes at 0° C. and then treated with tert-butylamine (0.48 g, 6.56 mmol, Aldrich, Milwaukee, Wis.). The reaction mixture was stirred for 1 hour at 0° C. and warmed to room temperature. The reaction mixture was then poured into Et2O, and washed sequentially with saturated aqueous NaHCO3 solution and saturated aqueous NaCl solution. The organic phase was dried over MgSO4, filtered, and concentrated. The crude residue was purified by chromatography (silica gel, 3:1 heptane/ethyl acetate) to give (S)-[2-[(1,1-dimethylethyl)amino]-2-oxo-1-(phenylmethyl)ethyl]-carbamic acid 1,1-dimethylethyl ester (2.65 g).
후처리
- stirringThe reaction mixture was stirred for 1 hour at 0° C.
- temperaturewarmed to room temperature
- washwashed sequentially with saturated aqueous NaHCO3 solution and saturated aqueous NaCl solution
- dry with materialThe organic phase was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe crude residue was purified by chromatography (silica gel, 3:1 heptane/ethyl acetate)
출처 및 근거
- ORD 기록
- ord-ffb257c994604a6284a9c938c8f41e60
- 출처 데이터셋
- uspto-grants-2001_11
- 특허 번호
- US06323243B1
연결된 노트
불러오는 중…