Allyl bromide → HCID 91611667, compound

HRID 1357505Notes

Reaction equation

HRID 1357505 reaction equation
[H-].[Na+].[CH2:3](Br)[CH:4]=[CH2:5].[C:7]([NH:10][C@@H:11]1[C@H:16]([OH:17])[CH2:15][C:14]([C:18]([O:20][CH3:21])=[O:19])=[CH:13][C@H:12]1[O:22][CH:23]([CH3:25])[CH3:24])(=[O:9])[CH3:8]>C1COCC1>[C:7]([NH:10][C@@H:11]1[C@H:16]([O:17][CH2:5][CH:4]=[CH2:3])[CH2:15][C:14]([C:18]([O:20][CH3:21])=[O:19])=[CH:13][C@H:12]1[O:22][CH:23]([CH3:25])[CH3:24])(=[O:9])[CH3:8]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 91616889HCID 91616889, compound

Product 1

HCID 91611667HCID 91611667, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60%, 35 mg, 0.875 mmol) and allyl bromide (0.051 mL, 0.589 mmol) were added to a 0° C. solution of Example 13L (80 mg, 0.295 mmol) in THF (15 mL). After stirring for 5 hours, the reaction mixture was quenched with saturated NH4Cl, and then extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried (MgSO4), filtered and concentrated. The concentrate was purified by flash chromatography using ethyl acetate to afford 83 mg (90%) of the desired product as a white solid.

Workup

  1. customthe reaction mixture was quenched with saturated NH4Cl
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by flash chromatography

Sources & evidence

ORD record
ord-04e49cde5ac64d988b9a9c2b4fd783ac
Source dataset
uspto-grants-2003_07
Patent number
US06593314B1

Reaction notes

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