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

HRID 2074969Notes

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 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 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-14dff8204f6541e0b6a0e1f3def74609
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919528B2

Reaction notes

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