Sodium hydride → HCID 86754826, compound

HRID 1603646Notes

Reaction equation

[CH3:1][C@H:2]1[C@H:5]([S:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[NH:4][C:3]1=[O:14].[H-].[Na+].Br[CH2:18][C:19](=[O:28])[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1>[CH3:1][C@H:2]1[C@H:5]([S:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:4]([CH2:18][C:19](=[O:28])[CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:3]1=[O:14]

Participants

Conditions

Temperature: -10 °C

Procedure

A solution of trans-3-methyl-4-(benzylthio)azetidin-2-one (0.73 g, 3.5 mmol) in dry THF (5 ml) was added dropwise over 5 minutes to a suspension of sodium hydride (60% dispersion in oil, 0.15 g, 3.8 mmol) in dry THF (10 ml) under a nitrogen atmosphere at -10° C. The mixture was stirred for 10 minutes at -10° C. and 1-bromo-4-phenylbutan-2-one (0.79 g, 3.5 mmol) in dry THF (10 ml) was added over 5 minutes at -10° C. The mixture was stirred at room temperature for 30 minutes and poured into ice/water. The layers were separated and the aqueous was extracted with ethyl acetate. The combined organics were washed with brine, dried (MgSO4) and evaporated to an oil. This was purified by flash chromatography on silica gel eluting with petroleum ether 40-60° C./ethyl acetate 3:1, 2:1 to give a colourless solid (0.34 g, 27%) mp 69-71° C.

Workup

stirringThe mixture was stirred at room temperature for 30 minutes
customThe layers were separated
extractionthe aqueous was extracted with ethyl acetate
washThe combined organics were washed with brine
dry with materialdried (MgSO4)
customevaporated to an oil
customThis was purified by flash chromatography on silica gel eluting with petroleum ether 40-60° C./ethyl acetate 3:1, 2:1

Sources & evidence

ORD record: ord-5e9bf3ba8f944cb884814645d3b93013
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05990102

Reaction notes

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