Sodium bis(trimethylsilyl)amide → HCID 67084600, compound

HRID 2103594Notes

Reaction equation

HRID 2103594 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[Br-].[CH3:12][C:13]([CH3:18])([CH3:17])[CH2:14][CH2:15][PH3+].[CH2:19]([O:21][C:22](=[O:33])[C:23]([C:25]1[CH:30]=[CH:29][C:28]([S:31][CH3:32])=[CH:27][CH:26]=1)=O)[CH3:20]>C(Cl)Cl.C1COCC1.C1COCC1>[CH2:19]([O:21][C:22](=[O:33])/[C:23](/[C:25]1[CH:30]=[CH:29][C:28]([S:31][CH3:32])=[CH:27][CH:26]=1)=[CH:15]/[CH2:14][C:13]([CH3:18])([CH3:17])[CH3:12])[CH3:20]

Participants

6

Reactant 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 2758911Ethyl 4-thiomethylbenzoylformateHCID 86605123HCID 86605123, compound

Product 1

HCID 67084600HCID 67084600, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

Add sodium bistrimethylsilylamide(4.67 mL, 2.0 M in THF, 9.35 mmol) to a solution of (3,3-Dimethyl-butyl) phosphonium bromide (4.00 g, 9.35 mmol)in CH2Cl2/THF at 0° C. Dissolve (4-methylsulfanyl-phenyl)-oxo-acetic acid ethyl ester (prepared as described by I. T. Barnish et. al. J. Med. Chem. 1981, 24, 399-404) in THF and add the resulting solution to the reaction mixture at 78° C. Stir at room temperature over-night. Add water and extract 3 X with dichloromethane, dry over sodium sulfate and concentrate under vacuum to afford 2.79 g raw material as a yellow oil. Further purify this material via silica gel chromatography, eluting with a gradient from 100% hexane to 50:50 hexane:dichlormethan to afford a colorless oil (700 mg). MS (m/e): 293 (M+H).

Workup

  1. extractionAdd water and extract 3 X with dichloromethane
  2. dry with materialdry over sodium sulfate
  3. concentrationconcentrate under vacuum
  4. customto afford 2.79 g raw material as a yellow oil
  5. customFurther purify this material via silica gel chromatography
  6. washeluting with a gradient from 100% hexane to 50:50 hexane

Sources & evidence

ORD record
ord-4c2d8dbc8a8140709fe029f90ffdd50b
Source dataset
uspto-grants-2009_08
Patent number
US07576108B2

Reaction notes

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