Dimethylformamide → HCID 53901059、化合物

HRID 1708596ノート

反応式

HRID 1708596 の反応式
[CH:1]1([N:7]([CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[C:8](=[O:17])[C:9]2[CH:14]=[CH:13][C:12](Br)=[C:11]([CH3:16])[CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([Li])(C)(C)C.CN(C)[CH:30]=[O:31]>C1COCC1>[CH:1]1([N:7]([CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[C:8](=[O:17])[C:9]2[CH:14]=[CH:13][C:12]([CH:30]=[O:31])=[C:11]([CH3:16])[CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 19754882HCID 19754882、化合物HCID 178418306HCID 178418306、化合物

生成物 1

HCID 53901059HCID 53901059、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a cold (-70° C.), stirred solution of 4-bromo-3-methylbenzoic acid N-cyclohexyl-N-cyclopentyl amide (4 g, 0.011 mol) in THF (40 mL) was added t-butyl lithium (13 mL of 1.7 M solution) via syringe over 10 min. The originally colorless solution became a dark red. Dimethylformamide (DMF) (884 mg) was added. The cold bath was removed and the reaction allowed to warm to 0° , during the course of which, the reaction became much lighter in color. The reaction was diluted with ethyl acetate, washed with 0.5 N KHSO4 and the organic layer was dried (Na2SO4). The drying agent was filtered, the filtrate concentrated in vacuo and the crude product purified by chromatography on silica gel using mixtures of ethyl acetate and hexane as eluents to give title compound of Step(a), m.p. 57°-59° C. Anal. Calcd for C20H27NO2 : C, 76.64; H, 8.68; N, 4.47. Found: C, 76.21; H, 8.71; N, 4.11.

後処理

  1. customThe cold bath was removed
  2. temperatureto warm to 0° , during the course of which
  3. additionThe reaction was diluted with ethyl acetate
  4. washwashed with 0.5 N KHSO4
  5. dry with materialthe organic layer was dried (Na2SO4)
  6. filtrationThe drying agent was filtered
  7. concentrationthe filtrate concentrated in vacuo
  8. customthe crude product purified by chromatography on silica gel using mixtures of ethyl acetate and hexane as eluents

出典と根拠

ORDレコード
ord-e20e4e8409aa4148bbcfedbd404ebcdb
出典データセット
uspto-grants-1994_10
特許番号
US05359073

反応ノート

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