Diisopropylamine → HCID 178472193、化合物

HRID 2075719ノート

反応式

HRID 2075719 の反応式
N(C(C)C)C(C)C.C([Li])CCC.[CH3:13][CH2:14][O:15][C:16]([CH3:18])=[O:17].[F:19][C:20]([F:30])([F:29])[C:21]([C:23]1[S:27][C:26]([SH:28])=[N:25][CH:24]=1)=[O:22]>C1COCC1>[CH2:14]([O:15][C:16](=[O:17])[CH2:18][C:21]([OH:22])([C:23]1[S:27][C:26]([SH:28])=[N:25][CH:24]=1)[C:20]([F:29])([F:19])[F:30])[CH3:13]

参加物

6

反応物 4

HCID 7912DiisopropylamineHCID 8857Ethyl AcetateHCID 178418339ButyllithiumHCID 178519847HCID 178519847、化合物

生成物 1

HCID 178472193HCID 178472193、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-78 °C

実験手順

iPr2NH (205 mg, 2.0 mmol) was dissolved in THF (3.5 mL) and cooled to −10° C. n-Butyllithium (2.5M, 0.81 mL, 2.0 mmol) was added dropwise, and the reaction was cooled to −78° C. EtOAc (179 mg, 2.0 μmmol) in THF (0.5 mL) was added, followed by 10a (188 mg, 0.9 mmol) in THF (10.5 mL), and the reaction was stirred at −78° C. for 1 hour. The reaction was warmed to −10° C. and quenched with 5% aqueous NH4Cl (10 mL). The aqueous layer was extracted with EtOAc, and the combined organic layers were washed with 1N HCl and brine, dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography (50% Et2O in hexanes) to give the desired product, 10b.

後処理

  1. additionwas added dropwise
  2. temperatureThe reaction was warmed to −10° C.
  3. customquenched with 5% aqueous NH4Cl (10 mL)
  4. extractionThe aqueous layer was extracted with EtOAc
  5. washthe combined organic layers were washed with 1N HCl and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel chromatography (50% Et2O in hexanes)

出典と根拠

ORDレコード
ord-d7eade74771040ea98b580918eabb288
出典データセット
uspto-grants-2011_04
特許番号
US07919621B2

反応ノート

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