Allyl Alcohol → HCID 58431049、化合物

HRID 1040476ノート

反応式

HRID 1040476 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 58431049HCID 58431049、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-b3292982ab6441609b16d74697bd8cd4
出典データセット
uspto-grants-2013_10
特許番号
US08552205B2

反応ノート

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