Triphenylphosphine → (S)-2-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionic acid tert-butyl ester

To a solution of (S)-2-(2-Oxo-2,3-dihydro-benzimidazol-1-yl)-propionic acid tert-butyl ester (0.3 g, 0.46 mmol), (4-Methyl-benzo[b]thiophen-3-yl)-methanol (0.12 g, 0.69 mmol), and triphenylphosphine (0.14 g, 0.55 mmol) was added dropwise DIAD (0.11 mL, 0.55 mmoL) at 0° C. The mixture was slowly warmed to room temperature and stirred for 2 h. The reaction mixture was diluted with ethyl acetate and washed with water (×2). The organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel prep TLC using 4:1 Hexanes:ethyl acetate as an eluent to afford 0.12 g (62%) of the desired product as a brownish oil. This product was not pure (˜70% pure by 1H-NMR), but was used for the next reaction without further purification.

1. washwashed with water (×2)
2. dry with materialThe organic phase was dried over Na2SO4
3. concentrationconcentrated
4. customThe resulting residue was purified by silica gel prep TLC

ORD 기록

ord-757ab58e91af4efa944fc82a4b3d346a

출처 데이터셋

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09150556B2