N,N-Bis(trimethylsilyl)trifluoroacetamide → HCID 57948924, 화합물

반응식

[NH2:1][C@@:2]([C:7]1[CH:12]=[C:11]([Br:13])[C:10]([F:14])=[CH:9][C:8]=1[F:15])([CH3:6])[CH2:3][CH2:4][OH:5].C[Si](N([Si](C)(C)C)C(=O)C(F)(F)F)(C)C.[C:31]([N:39]=[C:40]=[S:41])(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C1COCC1>[C:31]([NH:39][C:40]([NH:1][C@@:2]([C:7]1[CH:12]=[C:11]([Br:13])[C:10]([F:14])=[CH:9][C:8]=1[F:15])([CH3:6])[CH2:3][CH2:4][OH:5])=[S:41])(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

참가 물질

실험 절차

To a solution of (S)-3-amino-3-(5-bromo-2,4-difluoro-phenyl)-butan-1-ol (9.5 g, 34 mmoles, 1 equiv) in THF (50 mL) is added bis(trimethylsilyl)trifluoroacetamide (8.7 g, 34 mmol, 1 equiv). After 2 h, benzoyl isothiocyanate (5.5 g, 34 mmoles, 1 equiv) is added dropwise. The reaction is stirred 18 h, quenched with water, and extracted with ethyl acetate. The combined organic phases are extracted with 1 N HCl and saturated aqueous NaCl. The organic phase is dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the title compound (>95% yield, 90% purity as determined by LCMS): MS (m/z): 443, 445 (M+1).