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

HRID 1866609

反応式

HRID 1866609 の反応式
[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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-db22292baca7472face4cdcefbeb6fec
出典データセット
uspto-grants-2009_12
特許番号
US07629338B2

関連ノート

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