Triphenylphosphine → HCID 18617479、化合物

HRID 1264206ノート

反応式

HRID 1264206 の反応式
[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]

参加物

8

反応物 4

HCID 11776TriphenylphosphineHCID 18052Allyl chloroformate2 回HCID 516892Sodium BicarbonateHCID 18617612HCID 18617612、化合物

生成物 1

HCID 18617479HCID 18617479、化合物収率 61.7%

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-f79624cbefde49668129108c160a328f
出典データセット
uspto-grants-2003_04
特許番号
US06541505B1

反応ノート

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