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

HRID 1367132

Reaktionsgleichung

Reaktionsgleichung von HRID 1367132
[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

Komponenten

6

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-efb542ee37de4a34acd664741c7d8f46
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893079B2

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