Sodium hydride → HCID 68742224, compound

HRID 1942816Notes

Reaction equation

[C:1]1([C@H:7]2[CH2:11][O:10][C:9](=[O:12])[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:16][C:17]1[CH:29]=[CH:28][C:20]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:19][CH:18]=1.[Cl-].[NH4+]>C1COCC1>[O:12]=[C:9]1[N:8]([CH2:16][C:17]2[CH:29]=[CH:28][C:20]([C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22])=[CH:19][CH:18]=2)[C@@H:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:11][O:10]1

Participants

Conditions

Temperature: 0 °C

Procedure

(4S)-4-phenyl-1,3-oxazolidin-2-one (0.158 g, 0.968 mmol) was added to a stirred, 0° C. cooled mixture of sodium hydride (0.041 g, 1.014 mmol) in THF (2 ml) and the mixture was stirred at 0° C. for 15 min. 1,1-dimethylethyl 4-(bromomethyl)benzoate (0.25 g, 0.922 mmol) was then added and the reaction mixture was allowed to stirred at 0° C. for 30 min. Saturated ammonium chloride was added and the mixture was extracted with ethyl acetate (10 mL×2×). The combined organic fractions were dried over Na2SO4, filtered and the solvent was evaporated under reduced pressure to obtain 1,1-dimethylethyl 4-{[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]methyl}benzoate. The ester was taken to the next step without further purification.

Workup

temperaturecooled
stirringto stirred at 0° C. for 30 min
extractionthe mixture was extracted with ethyl acetate (10 mL×2×)
dry with materialThe combined organic fractions were dried over Na2SO4
filtrationfiltered
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-d545fdc9f3734c2f8bc9641645005893
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389553B2

Reaction notes

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