Potassium Carbonate → HCID 86658713, compound

HRID 2368149Notes

Reaction equation

HRID 2368149 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C@@H:13]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH3:14])=[CH:7][CH:6]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:12][C@@H:13]([NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH3:14])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 57517512HCID 57517512, compound

Product 1

HCID 86658713HCID 86658713, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-({(2S)-2-[(tert-butoxycarbonyl)amino]propyl}oxy)phenyl acetate (70 g), potassium carbonate (156 g) and methanol (800 mL) was stirred at room temperature for 3 days. The reaction mixture was concentrated under reduced pressure, and the obtained residue was neutralized with aqueous citric acid solution, and diluted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (40.5 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b3a9de438bd047e8b302d7cbccd3f6d4
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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