Allyl Alcohol → HCID 53841977, compound

HRID 482579Notes

Reaction equation

HRID 482579 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]([OH:15])=[O:14])[CH:10]([CH3:12])[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:16](O)[CH:17]=[CH2:18].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C(Cl)(Cl)Cl>[CH2:18]([O:14][C:13](=[O:15])[C@H:9]([CH:10]([CH3:11])[CH3:12])[NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH:17]=[CH2:16]

Participants

6

Reactant 4

HCID 7858Allyl AlcoholHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 83693Boc-L-Valine

Product 1

HCID 53841977HCID 53841977, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of N-(tert-butyloxycarbonyl)-L-valine (10.53 g; 48.5 mmol) and allyl alcohol (33 mL; 49 mmol) in 150 mL CHCl3 at 0° C. was added HOBt (8.53 g; 63.1 mmol) then EDCI (13.88 g, 72.4 mmol). The final mixture was stirred at 4° C. for 12 h then poured in to 100 mL NH4OAc (25%). The organic phase was separated. The aqueous phase was washed with 50 mL of CHCl3. The organic phases were combined, dried over Na2SO4, concentrated and flash chromatographed on silica gel (hexane/EtOAc 9:1) to yield 5.10 g (41 %) of the title compound.

Workup

  1. customThe organic phase was separated
  2. washThe aqueous phase was washed with 50 mL of CHCl3
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customflash chromatographed on silica gel (hexane/EtOAc 9:1)

Sources & evidence

ORD record
ord-92f6ebbd3e2245f783767e94a8591393
Source dataset
uspto-grants-1998_08
Patent number
US05798442

Reaction notes

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