反应详情

A mixture of tert-butyl 2-(3-aminophenoxy)ethylcarbamate (3) (210 mg, 1.1 mmol), 2-pentylsulfonyl chloride (4) (0.17 ml, 1.1 mmol) and DMAP (20 mg) in pyridine (5 ml) was stirred at room temperature under argon for 15 hours. The solvent was evaporated under reduced pressure. The residue was partitioned between EtOAc and 0.5 N HCl aq. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. Purification by flash chromatography (40 to 60% EtOAc-hexanes gradient) gave tert-butyl 2-(3-(1-methylbutylsulfonamido)phenoxy)ethylcarbamate (5) as light yellow oil. Yield (160 mg, 46%). 1H NMR (400 MHz, CDCl3) δ 7.20 (t, J=8.0 Hz, 1H), 6.75-6.82 (m, 1H), 6.73-6.75 (m, 1H), 6.64-6.67 (m, 1H), 6.37 (bs, 1H), 4.96 (bs, 1H), 3.99 (t, J=6.0 Hz, 2H), 3.51 (q, J=6.0 Hz, 2H), 3.11-3.18 (m, 1H), 1.91-2.0 (m, 1H), 1.53-1.60 (m, 2H), 1.44 (s, 9H), 1.23-1.37 (m, 4H), 0.88-0.91 (m, 3H).

1. customThe solvent was evaporated under reduced pressure
2. customThe residue was partitioned between EtOAc and 0.5 N HCl aq. The organic layer
3. washwas washed with brine
4. dry with materialdried over Na2SO4
5. concentrationconcentrated under reduced pressure
6. customPurification by flash chromatography (40 to 60% EtOAc-hexanes gradient)