Benzyl Alcohol → HCID 11626340, 화합물

HRID 1363102노트

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HRID 1363102 반응식
[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

참가 물질

6

반응물 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 59778157HCID 59778157, 화합물

생성물 1

HCID 11626340HCID 11626340, 화합물수율 86%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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%).

후처리

  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%

출처 및 근거

ORD 기록
ord-2eecd6913563471a8fce578826633e17
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07884113B2

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