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

HRID 1744809Notes

Reaction equation

[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]CCCC.[C:19](Cl)(=[O:26])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>C1COCC1>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:19](=[O:26])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 10 °C

Procedure

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). MH+290.

Workup

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

Sources & evidence

ORD record: ord-6c8d738a13184849b93dc495a25095ed
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07019003B2

Reaction notes

Loading…