Sodium Chloride → 3-(2-Ethoxyethanoyl)-4-benzyloxazolidin-2-one

HRID 585008Notes

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.CCCCCC.C([Li])CCC.[CH2:25]([O:27][CH2:28][C:29](Cl)=[O:30])[CH3:26].[Cl-].[Na+]>C1COCC1>[CH2:25]([O:27][CH2:28][C:29]([N:9]1[CH:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:12][O:11][C:10]1=[O:13])=[O:30])[CH3:26]

Participants

Conditions

Temperature: -78 °C

Procedure

36.7 g (207 mmol) of (S)-4-benzyloxazolidin-2-one in 800 ml of THF are introduced into a round-bottomed flask under a stream of nitrogen. The reaction medium is cooled to −78° C. and 83 ml (207 mmol) of 2.5M n-butyllithium hexane are added dropwise. 30 minutes later, 25.4 g (207 mmol) of ethoxyacetyl chloride obtained in Example 81(b) are added, at −78° C. The reaction medium is stirred for 24 hours and then poured into saturated aqueous sodium chloride solution and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and evaporated. After purification by chromatography on a column of silica eluted with a heptane/ethyl acetate mixture (6/4), 30.6 g (56%) of the expected product are obtained in the form of an orange-colored oil.

Workup

extractionextracted with ethyl acetate
dry with materialThe organic phase is dried over magnesium sulfate
filtrationfiltered
customevaporated
customAfter purification by chromatography on a column of silica
washeluted with a heptane/ethyl acetate mixture (6/4), 30.6 g (56%) of the expected product
customare obtained in the form of an orange-colored oil

Sources & evidence

ORD record: ord-87b9334d6a78453ab58a80b7a1cff62e
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06927228B2

Reaction notes

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