Diisopropylethylamine → N-{(1S)-1-[(4-Bromophenyl)methyl]-3-hydroxypropyl)-3-cyano-4-[(1-methylethyl)oxy]benzamide

To a suspension of (3S)-3-Amino-4-(4-bromophenyl)-1-butanol hydrochloride (1.80 g, 6.42 mmol) in dry DMF (32 mL) was added N,N-diisopropylethyl amine (2.49 g, 19.3 mmol) and the resultant clear solution was stirred for 3 min. 3-Cyano-4-[(1-methylethyl)oxy]benzoic acid (1.45 g, 7.06 mmol) and HBTU (2.68 g, 7.06 mmol) were added and the reaction was stirred at rt under nitrogen. After 1.5 h, the reaction mixture was quenched with water (50 mL) and extracted with EtOAc (3×30 mL). The extracts were dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (75% EtOAc/hexanes) to give 2.18 g (78%) of the title compound as a white solid. LC/MS (ES) m/e 431.2 (M+H)+.

1. stirringthe reaction was stirred at rt under nitrogen
2. waitAfter 1.5 h
3. customthe reaction mixture was quenched with water (50 mL)
4. extractionextracted with EtOAc (3×30 mL)
5. dry with materialThe extracts were dried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by silica gel chromatography (75% EtOAc/hexanes)

ORD 기록

ord-2d6f9e940c9144b1922eaf86d118845a

출처 데이터셋

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07582668B2