Benzyl Alcohol → HCID 11626340、化合物

HRID 1363102ノート

反応式

HRID 1363102 の反応式
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]([F:21])([F:20])[F:19])=[CH:15][CH:16]=2)[CH2:11][CH:10](C(O)=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:32])C=CC=CC=1.C([N:44]([CH2:47]C)CC)C.[CH2:49]([OH:56])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>O1CCOCC1>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]([F:19])([F:20])[F:21])=[CH:15][CH:16]=2)[CH2:11][CH:10]([NH:44][C:47](=[O:32])[O:56][CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 59778157HCID 59778157、化合物

生成物 1

HCID 11626340HCID 11626340、化合物収率 86%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

To a solution of 149D) (345 mg, 1.029 mmol) in dioxane (3.5 mL) was added diphenylphosphoryl azide (244 μL, 1.133 mmol) and triethylamine (170 μL, 1.236 mmol). The reaction mixture was stirred at RT for 20 min, then benzylalcohol (130 μL, 1.236 mmol) was added. The reaction was heated at 100° C. for 7 h. After cooling to RT, the reaction mixture was concentrated in vacuo, and the residue partitioned between EtOAc and water. The separated organic layer was washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was chromatographed (silica gel) eluting with EtOAc/hexane 0-40% to afford 149E as a clear oil (390 mg, 86%).

後処理

  1. temperatureThe reaction was heated at 100° C. for 7 h
  2. temperatureAfter cooling to RT
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. customthe residue partitioned between EtOAc and water
  5. washThe separated organic layer was washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed (silica gel)
  9. washeluting with EtOAc/hexane 0-40%

出典と根拠

ORDレコード
ord-2eecd6913563471a8fce578826633e17
出典データセット
uspto-grants-2011_02
特許番号
US07884113B2

反応ノート

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