Iodoethane → HCID 22494032, compound

HRID 1816603Notes

Reaction equation

HRID 1816603 reaction equation
C([C:3]([O:24][CH:25]([CH3:27])[CH3:26])([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:9]=1)[C:4]([OH:6])=[O:5])C.I[CH2:29][CH3:30].C(=O)([O-])[O-].[K+].[K+].[C:37](OCC)(=O)[CH3:38]>CN(C)C=O>[C:20]([O:19][C:17]([NH:16][CH2:15][C:10]1[CH:9]=[C:8]([CH2:7][CH:3]([O:24][CH:25]([CH3:26])[CH3:27])[C:4]([O:6][CH2:29][CH3:30])=[O:5])[CH:13]=[CH:12][C:11]=1[O:14][CH2:37][CH3:38])=[O:18])([CH3:22])([CH3:23])[CH3:21]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 22494120HCID 22494120, compound

Product 1

HCID 22494032HCID 22494032, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

795 mg of ethyl 3-(3-[(tertiary butoxycarbonyl)amino]methyl-4-hydroxyphenyl)-2-isopropoxypropionic acid was dissolved in 2 ml N,N-dimethylformamide, and 0.3 ml iodoethane and 200 mg potassium carbonate were successively added. After stirring at 50° C. for 4 hours, the reaction mixture was diluted with ethyl acetate, The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and the solvent was evapoarated. The residue was purified by silica gel column chromatography, and from fractions eluted with hexane-ethyl acetate (8:1), 185 mg of ethyl 3-(3-[(tertiary butoxycarbonyl)amino]methyl-4-ethoxyphenyl)-2-isopropoxypropionate was obtained.

Workup

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe residue was purified by silica gel column chromatography
  4. washfrom fractions eluted with hexane-ethyl acetate (8:1)

Sources & evidence

ORD record
ord-31a33ce103bd4d1dbb78675bfc4e0214
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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