Trimethylsilyldiazomethane → Methyl 2-{[2-(3,5-difluorophenyl)-2-oxoethyl]thio}-2-methylpropanoate

HRID 1864813

Reaction equation

HRID 1864813 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9](=[O:18])[CH2:10][S:11][C:12]([CH3:17])([CH3:16])[C:13]([OH:15])=[O:14])[CH:5]=[C:6]([F:8])[CH:7]=1.[CH3:19][Si](C=[N+]=[N-])(C)C>CO.CCOCC.O>[F:1][C:2]1[CH:3]=[C:4]([C:9](=[O:18])[CH2:10][S:11][C:12]([CH3:16])([CH3:17])[C:13]([O:15][CH3:19])=[O:14])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 669733052-{[2-(3,5-Difluorophenyl)-2-oxoethyl]thio}-2-methylpropanoic acid

Product 1

HCID 66973283Methyl 2-{[2-(3,5-difluorophenyl)-2-oxoethyl]thio}-2-methylpropanoate

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2-{[2-(3,5-difluorophenyl)-2-oxoethyl]thio}-2-methylpropanoic acid from Step A (400. mg, 1.46 mmol) in MeOH (3 mL), was added trimethylsilyldiazomethane (2 M in hexanes) until yellow color persists. The reaction mixture was stirred for an additional twenty minutes. The reaction mixture was diluted with ether (30 mL) and water (10 mL). The organics were washed with 5% sodium bicarbonate and then with saturated brine. The organics were dried over sodium sulfate, filtered, and concentrated in vacuo to give a residue. This residue was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:Hexanes-40:60 to 90:10, to give the title compound. MS: m/z=229 (M−CO2Me).

Workup

  1. washThe organics were washed with 5% sodium bicarbonate
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a residue
  6. customThis residue was purified by silica gel chromatography
  7. washeluting with a gradient of CH2Cl2

Sources & evidence

ORD record
ord-69336b16ee384dd68d3fcc2f60ba1aee
Source dataset
uspto-grants-2009_12
Patent number
US07625901B2

Linked notes

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