Allyl Alcohol → HCID 58431049, 화합물

HRID 1040476노트

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HRID 1040476 반응식
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1(C(O)=O)[CH2:9][CH2:8]1.C1(P([N:27]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[CH2:30]([OH:33])[CH:31]=[CH2:32].CCO[C:37](C)=[O:38]>C1(C)C=CC=CC=1.O>[CH2:30]([O:33][C:37](=[O:38])[NH:27][C:7]1([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][N:1]=2)[CH2:8][CH2:9]1)[CH:31]=[CH2:32]

참가 물질

7

반응물 4

HCID 7858Allyl AlcoholHCID 8857Ethyl AcetateHCID 199401P,P-Diphenylphosphinic azideHCID 584310521-(Pyrazin-2-yl)cyclopropane-1-carboxylic acid

생성물 1

HCID 58431049HCID 58431049, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

실험 절차

To a solution of 1-Pyrazin-2-yl-cyclopropanecarboxylic acid (111 mg, 0.676 mmol) in dry toluene (1.5 mL) was added TEA (0.11 mL, 0.81 mmol) followed by diphenylphosphoryl azide (DPPA, 0.16 mL, 0.74 mmol). The reaction was stirred for 1 h at rt. Allyl alcohol (0.2 mL) was added via syringe and the reaction was heated to 90° C. for 3 h. After cooling to room temperature, the reaction was diluted with water (6 mL) and EtOAc (4 mL). The layers were separated and the water layer was extracted with EtOAc (3×4 mL). The combined organic layers were dried over Na2SO4 and concentrated to give a black residue that was purified by flash chromatography (silica, 40→50% EtOAc/hexanes) to give 67 mg of the title compound as a light orange oil, m/z 220.52 [M+1]+.

후처리

  1. temperaturethe reaction was heated to 90° C. for 3 h
  2. temperatureAfter cooling to room temperature
  3. customThe layers were separated
  4. extractionthe water layer was extracted with EtOAc (3×4 mL)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated
  7. customto give a black residue that
  8. customwas purified by flash chromatography (silica, 40→50% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-b3292982ab6441609b16d74697bd8cd4
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552205B2

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