HCID 59556159, compound → HCID 59556099, compound

HRID 1809847Notes

Reaction equation

HRID 1809847 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[C:16](=[O:17])[CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:25]([Mg]Br)[CH:26]=[CH2:27]>C1COCC1>[CH2:27]([C:16]1([OH:17])[C@@H:12]([NH:11][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:13][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:15]1)[CH:26]=[CH2:25]

Participants

4

Reactant 2

HCID 59556159HCID 59556159, compoundHCID 178455850HCID 178455850, compound

Product 1

HCID 59556099HCID 59556099, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.44 g of the ketone of step B in 20 mL of anhydrous THF cooled at 0° C. was added a solution of 6.2 mL of 1 M allyl magnesium bromide. The color turned dark right away. After being stirred at room temperature overnight, the reaction mixture was quenched with 50/50 mL of EtOAc/water. Water phase was extracted twice with EtOAc. The combined organic phase was dried over Na2SO4 and concentrated under vacuum. Column chromatography on silica gel using 3:1˜2:1 hexane/EtOAc as eluent provided 0.85 g of the title compound. MS (M+H)+377.

Workup

  1. customthe reaction mixture was quenched with 50/50 mL of EtOAc/water
  2. extractionWater phase was extracted twice with EtOAc
  3. dry with materialThe combined organic phase was dried over Na2SO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9fc704e5aa924ce5a186aa307b11f0d2
Source dataset
uspto-grants-2013_01
Patent number
US08362003B2

Reaction notes

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