Diethyl Ether → HCID 20312416, compound

HRID 2420007Notes

Reaction equation

HRID 2420007 reaction equation
[C:1]1([Li])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:8]([O:12][C:13](=[O:27])[CH:14](OC(=O)C)[NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:9][CH2:10][CH3:11].CCOCC>O>[CH2:8]([O:12][C:13](=[O:27])[CH:14]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 20312395HCID 20312395, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 20312416HCID 20312416, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution containing 2.4 mmol. of phenyl lithium in benzene-ether was added dropwise at -78° under argon to a solution of 700 mg. (2.4 mmol.) of N-t-butoxycarbonyl-2-acetoxyglycine n-butyl ester in 15 ml. of dry ether. The mixture was stirred for 2 hours at -78°, then for 1 hour at 25°. The mixture was diluted with water, the layers were separated and the ether layer was washed with water, dried (Na2SO4) and concentrated in vacuo. The residue was chromatographed on silica gel with methylene chloride to give a crude product which was rechromatographed on basic alumina to give the title compound.

Workup

  1. additionA solution containing 2.4 mmol
  2. waitfor 1 hour at 25°
  3. customthe layers were separated
  4. washthe ether layer was washed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica gel with methylene chloride
  8. customto give a crude product which
  9. customwas rechromatographed on basic alumina

Sources & evidence

ORD record
ord-57a246bbf6234f29895fe96e7085aad2
Source dataset
uspto-grants-1978_08
Patent number
US04108854

Reaction notes

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