Cyanamide → 4-(4-Fluorophenoxy)phenethyl carbamimidate

HRID 474641노트

반응식

HRID 474641 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][OH:17])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[N:18]#[C:19][NH2:20].FC(F)(F)S(O)(=O)=O>C1COCC1>[C:19](=[NH:18])([O:17][CH2:16][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:10][CH:11]=1)[NH2:20]

참가 물질

5

반응물 3

HCID 9864CyanamideHCID 62406Trifluoromethanesulfonic acidHCID 677754954-(4-Fluorophenoxy)phenethyl alcohol

생성물 1

HCID 679525344-(4-Fluorophenoxy)phenethyl carbamimidate수율 32.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-{4-[(4-fluorophenyl)oxy]phenyl}ethanol (750 mg, 3.23 mmol) and cyanamide (149 mg, 3.55 mmol) in THF (15 mL) was added trifluoromethanesulfonic acid (0.344 mL, 3.88 mmol) at 0° C. The reaction mixture was stirred at room temperature overnight. After removing the solvent, the residue was diluted with water, extracted with DCM. The organic phase was dried over sodium sulfate, filtered, and concentrated. Purification via reverse phase flash chromatography then afforded the title compound (290 mg, 1.057 mmol, 32.7% yield).

후처리

  1. customAfter removing the solvent
  2. additionthe residue was diluted with water
  3. extractionextracted with DCM
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification via reverse phase flash chromatography

출처 및 근거

ORD 기록
ord-cefec08e60fc449084868357a1528767
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637536B2

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