Dimethylformamide → HCID 53901059, 화합물

HRID 1708596노트

반응식

HRID 1708596 반응식
[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

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 19754882HCID 19754882, 화합물HCID 178418306HCID 178418306, 화합물

생성물 1

HCID 53901059HCID 53901059, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e20e4e8409aa4148bbcfedbd404ebcdb
출처 데이터셋
uspto-grants-1994_10
특허 번호
US05359073

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