Allyl Alcohol → HCID 58080850, compound

HRID 1845946Notes

Reaction equation

HRID 1845946 reaction equation
[CH2:1](O)[CH:2]=[CH2:3].N(C(OC(C)C)=O)=NC(OC(C)C)=O.[CH2:19]([N:22]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:23][C@H:24]([NH:26][S:27]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[N+:36]([O-:38])=[O:37])(=[O:29])=[O:28])[CH3:25])[CH:20]=[CH2:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.O>[CH2:3]([N:26]([C@H:24]([CH3:25])[CH2:23][N:22]([CH2:19][CH:20]=[CH2:21])[C:39]([O:41][C:42]([CH3:44])([CH3:43])[CH3:45])=[O:40])[S:27]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[N+:36]([O-:38])=[O:37])(=[O:28])=[O:29])[CH:2]=[CH2:1]

Participants

7

Reactant 4

HCID 7858Allyl AlcoholHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 58080843HCID 58080843, compound

Product 1

HCID 58080850HCID 58080850, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.4 mL of allyl alcohol and 1.5 mL of diisopropyl azodicarboxylate were added dropwise at room temperature in an argon atmosphere to a solution containing 1 g of the compound obtained in Step 2 and 2 g of triphenylphosphine dissolved in 100 mL of tetrahydrofuran, and then reacted for 16 hours. The reaction solution was diluted with water, followed by extraction with ethyl acetate (100 mL×2). Then, the extract was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated, and the obtained crude product was purified by silica gel column chromatography (acetone:hexane=1:2) to obtain 550 mg of the compound of interest as a colorless oil (50%).

Workup

  1. customreacted for 16 hours
  2. extractionfollowed by extraction with ethyl acetate (100 mL×2)
  3. dry with materialThen, the extract was dried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated
  6. customthe obtained crude product
  7. customwas purified by silica gel column chromatography (acetone:hexane=1:2)

Sources & evidence

ORD record
ord-9e427d44ce394ac78fd526e4375cb523
Source dataset
uspto-grants-2015_02
Patent number
US08951997B2

Reaction notes

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