反应详情

To a solution of (S)-2-(tert-butoxycarbonylamino)-3-phenylpropanoic acid (1.03 g, 3.81 mmol) in THF (70 mL), are added DCC (1.03 g, 4.91 mmol), HOBt (660 mg, 4.90 mmol) and 3(R)-quinuclidinol (1.18 g, 9.48 mmol) and the resulting mixture is stirred for 12 hours at RT under nitrogen flowstream (LC-MS monitoring: complete conversion). The solvent is evaporated and the residue is partitioned between EtOAc (100 mL) and 2M K2CO3 (50 mL); the organic layer is separated, washed with brine and dried over Na2SO4. The resulting crude is purified by flash chromatography (DCM/MeOH=95/5, 0.1% NH3 (aq.)) to obtain 1.12 g of I19 (80% yield).

1. customThe solvent is evaporated
2. customthe residue is partitioned between EtOAc (100 mL) and 2M K2CO3 (50 mL)
3. customthe organic layer is separated
4. washwashed with brine
5. dry with materialdried over Na2SO4
6. customThe resulting crude is purified by flash chromatography (DCM/MeOH=95/5, 0.1% NH3 (aq.))
7. customto obtain 1.12 g of I19 (80% yield)