Heptanoyl chloride → (4S)-4-Benzyl-3-heptanoyl-1,3-oxazolidin-2-one

Temperature

10 °C

To a solution of (S)-(−)-4-benzyl-2-oxazolidinone (3.3 g, 18.6 mmol) in THF (50 mL) at −78° C. was added dropwise n-BuLi (7.4 mL, 2.5M solution in hexane, 18.6 mmol). After stirring for 30 min at the same temperature, the reaction mixture was then treated with heptanoyl chloride (2.76 g, 18.6 mmol). The reaction mixture was stirred and allowed to warm to 10° C. over 5 h, and then quenched with saturated aqueous NH4Cl solution (100 mL). The aqueous layer was extracted with EtOAc (100 mL×2). The combined organic layers were washed with brine, and dried over MgSO4. Removal of the solvent under reduced pressure yielded 4.63 g (86%) of the title compound. 1H NMR (400 MHz, CDCl3) δ 7.37–7.22 (m, 5H), 4.69 (m, 1H), 4.19 (m, 2H), 3.31 (dd, J=13.4, 3.3 Hz, 1H), 2.95 (m, 2H), 2.79 (dd, J=13.4, 9.7 Hz, 1H), 1.71 (m, 2H), 1.42–1.32 (m, 6H), 0.92 (t, J=6.8 Hz, 3H). Mass spectrum ES+: 290 [M+H]+.

1. stirringThe reaction mixture was stirred
2. customquenched with saturated aqueous NH4Cl solution (100 mL)
3. extractionThe aqueous layer was extracted with EtOAc (100 mL×2)
4. washThe combined organic layers were washed with brine
5. dry with materialdried over MgSO4
6. customRemoval of the solvent under reduced pressure

ORD record

ord-5aec3a8efa294ffeb55e110517bce09e

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07166624B2