Allyl bromide → HCID 85970139, compound

HRID 2215252Notes

Reaction equation

HRID 2215252 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[CH2:5][NH:6][C:7](=[O:11])[CH:8]([CH3:10])[CH3:9])[CH3:2].C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH3:23][CH2:24][CH2:25]CCC.C(Br)C=C>C1COCC1>[CH2:1]([O:3][C:4](=[O:12])[CH:5]([NH:6][C:7](=[O:11])[CH:8]([CH3:9])[CH3:10])[CH2:25][CH:24]=[CH2:23])[CH3:2]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 8058HexaneHCID 2733832Lithium HexamethyldisilazideHCID 4674605HCID 4674605, compound

Product 1

HCID 85970139HCID 85970139, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

11.74 g of the above prepared isobutyrylamino-acetic acid ethyl ester (67.78 mmol) was dissolved in 250 ml of abs. THF and cooled down to −78°. 139 ml of 1M lithium hexamethyldisilazide in hexane (2.05 eq.) were added within 30 Min. via dropping funnel. After keeping the yellow suspension for additional 30 Min. at −78°, 6.021 ml of allyl bromide (1.05 eq.) was added and stirring continued for 15 Min. at the same temperature and for 30 Min. at 0°. Pouring of the homogeneous reaction mixture onto crashed ice/HCl, twofold extraction with AcOEt, twofold washing with water and brine, drying over magnesium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=7/3) afforded. 11.70 g of the title compound as pale-yellow oil.

Workup

  1. dissolutionwas dissolved in 250 ml of abs
  2. customat 0°
  3. additionPouring of the homogeneous reaction mixture
  4. extractionice/HCl, twofold extraction with AcOEt
  5. washtwofold washing with water and brine
  6. dry with materialdrying over magnesium sulfate, and evaporation of the solvents
  7. customafforded

Sources & evidence

ORD record
ord-5b4498de7d6c4c0dbeba30c0e34ebdc4
Source dataset
uspto-grants-2006_09
Patent number
US07109225B2

Reaction notes

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