Allyl bromide → HCID 67029021, compound

HRID 2040017Notes

Reaction equation

HRID 2040017 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH:14]1[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16][CH2:15]1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:23](Br)[CH:24]=[CH2:25]>CN(C=O)C>[CH2:25]([O:20][CH:17]1[CH2:16][CH2:15][CH:14]([CH2:13][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C:10]([OH:12])=[O:11])[CH2:19][CH2:18]1)[CH:24]=[CH2:23]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 67028705HCID 67028705, compound

Product 1

HCID 67029021HCID 67029021, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 5.42 g (18.86 mmol) of (S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-cyclohexyl)propionic acid in 20 ml of DMF was added dropwise over the course of 30 min to a suspension of 1.89 g (47.14 mmol) of 60% sodium hydride in 20 ml of DMF at 0° C. Then 2.28 g (18.86 mmol) of allyl bromide were added, and the mixture was warmed to RT and then stirred for 3 h. It was cautiously quenched with water and concentrated. The residue was dissolved in water and washed with ethyl acetate. The aqueous phase was adjusted to pH 2 with 6M HCl and extracted with ethyl acetate. The organic phase was dried over Na2SO4, filtered and concentrated. The title compound obtained in this way was reacted further without further purification.

Workup

  1. customIt was cautiously quenched with water
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in water
  4. washwashed with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0ab89c34c4fc4a0fb7aa945cbdf725eb
Source dataset
uspto-grants-2013_11
Patent number
US08580777B2

Reaction notes

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