Triphenylphosphine → HCID 18617479, 화합물

HRID 1264206노트

반응식

HRID 1264206 반응식
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][CH2:13][N:14]=[N+]=[N-])[CH:10]=2)[NH:5][CH:4]=1)#[N:2].C1(P([C:30]2[CH:35]=[CH:34]C=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:36](=O)([OH:38])[O-:37].[Na+].Cl[C:42]([O:44][CH2:45][CH:46]=[CH2:47])=[O:43]>C1COCC1.C(OCC)(=O)C.O>[CH2:45]([O:44][C:42]([N:5]1[C:6]2[C:11](=[CH:10][C:9]([CH2:12][CH2:13][NH:14][C:36]([O:38][CH2:34][CH:35]=[CH2:30])=[O:37])=[CH:8][CH:7]=2)[C:3]([C:1]#[N:2])=[CH:4]1)=[O:43])[CH:46]=[CH2:47]

참가 물질

8

반응물 4

HCID 11776TriphenylphosphineHCID 18052Allyl chloroformate2회HCID 516892Sodium BicarbonateHCID 18617612HCID 18617612, 화합물

생성물 1

HCID 18617479HCID 18617479, 화합물수율 61.7%

시약·촉매·용매 3

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 1.89 g (8.95 mmol) 3-cyano-5-(2-azidoethyl)-indole (reference example 3) and 2.58 g (9.85 mmol) triphenylphosphine in 40 mL THF is stirred overnight to give a white precipitate. To this is added 0.32 mL H2O, and stirring is continued overnight. Then 4.75 g (44.8 mmol) sodium bicarbonate and 15 mL H2O, followed by 2.1 mL (20 mmol) allyl chloroformate, is added. After stirring overnight another 2 mL allyl chloroformate is added, followed by stirring overnight. The reaction mixture is diluted with ethyl acetate and washed with distilled water. The organic layer is concentrated, and the resulting residue chromatographed (3:1, then 1:1 hexane:ethyl acetate) to provide the product as a white solid in 61.7% yield. 1H NMR (CDCl3): δ 2.96 (2H, t, J=7.0 Hz), 3.50 (2H, m), 4.56 (2H, d, J=5.4 Hz), 4.97 (2H, d, J=5.9 Hz), 5.25 (2H, m), 5.46 (2H, m), 5.91 (1H, m), 6.06 (1H, m), 7.31 (1H, d, J=8.6 Hz), 7.54 (1H, s), 8.14 (1H, d, J=8.6 Hz), 8.15 (1H, s). MS (EI) m/z 353 M+, 268 (M−CO2Allyl)+.

후처리

  1. customto give a white precipitate
  2. additionis added
  3. additionis added
  4. stirringby stirring overnight
  5. washwashed with distilled water
  6. concentrationThe organic layer is concentrated
  7. customthe resulting residue chromatographed (3:1

출처 및 근거

ORD 기록
ord-f79624cbefde49668129108c160a328f
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06541505B1

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