Sodium hydride → HCID 10906020, compound

HRID 984430Notes

Reaction equation

HRID 984430 reaction equation
[CH3:1][CH:2]([C:9]([O:11][CH2:12][CH:13]=[CH2:14])=[O:10])[C:3]([O:5][CH2:6][CH:7]=[CH2:8])=[O:4].[H-].[Na+].[Si:17]([O:24][C@@H:25]([C@H:27]1[C@H:30](SC2C=CC=CC=2)[NH:29][C:28]1=[O:38])[CH3:26])([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].[Cl-].[NH4+]>O1CCCC1>[Si:17]([O:24][C@@H:25]([C@@H:27]1[C@@H:30]([C:2]([C:9]([O:11][CH2:12][CH:13]=[CH2:14])=[O:10])([C:3]([O:5][CH2:6][CH:7]=[CH2:8])=[O:4])[CH3:1])[NH:29][C:28]1=[O:38])[CH3:26])([C:20]([CH3:21])([CH3:22])[CH3:23])([CH3:18])[CH3:19]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 11084811HCID 11084811, compoundHCID 57099208HCID 57099208, compound

Product 1

HCID 10906020HCID 10906020, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of diallyl 2-methylmalonate (396 mg, 2 mmol) in tetrahydrofuran (2 ml) was added dropwise to a suspension of sodium hydride (80 mg, 2 mmol) in tetrahydrofuran (5 ml) under an argon stream at 0° C., and the solution mixture was stirred for 5 min and admixed with cuprous bromide dimethylsulfide complex (411 mg, 2 mmol), followed by stirring for 30 min at the same temperature, addition of a solution of (3R,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-phenylthio-2-azetidinone (338 mg, 1 mmole) in tetrahydrofuran (3 ml) and stirring for 1 hour. The reaction solution was admixed with aqueous saturated ammonium chloride solution and extracted with ethyl acetate. The ethyl acetate layer was dried over magnesium sulfate and concentrated under reduced pressure, and the residue was purified by column chromatography (10 g of silica gel; a 8/1 mixture of n-hexane/ethyl acetate) to give 392 mg (92%) of the subject compound in the form of colorless crystals.

Workup

  1. stirringstirring for 1 hour
  2. extractionextracted with ethyl acetate
  3. dry with materialThe ethyl acetate layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customthe residue was purified by column chromatography (10 g of silica gel
  6. additiona 8/1 mixture of n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-9407208f648249568bb96afc2f20183a
Source dataset
uspto-grants-2005_03
Patent number
US06867297B1

Reaction notes

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