Propionic Acid → HCID 70159372, compound

HRID 2227283Notes

Reaction equation

HRID 2227283 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][C@H:8]1[CH2:12][C@@H:11]([CH3:13])[N:10]([CH2:14][CH:15](O)[CH:16]=[CH:17][C:18]2[CH:19]=[N:20][C:21]([CH3:24])=[N:22][CH:23]=2)[C:9]1=[O:26])([CH3:4])([CH3:3])[CH3:2].[C:28]([OH:32])(=[O:31])[CH2:29]C.[CH2:33](C(CC)(CC)C([O-])([O-])[O-])[CH3:34]>C(OCC)(=O)C>[CH2:33]([O:32][C:28](=[O:31])[CH2:29][C@@H:17]([C:18]1[CH:19]=[N:20][C:21]([CH3:24])=[N:22][CH:23]=1)[CH:16]=[CH:15][CH2:14][N:10]1[C@H:11]([CH3:13])[CH2:12][C@H:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:27])[C:9]1=[O:26])[CH3:34]

Participants

5

Reactant 3

HCID 1032Propionic AcidHCID 21875354TriethylorthoaceateHCID 70160165HCID 70160165, compound

Product 1

HCID 70159372HCID 70159372, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of 5-2 (300 mg) and propionic acid (5 mg) in triethylorthoacetate (6 mL) was heated at 140° C. for 3 hours, then cooled to ambient temperature. The mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate, saturated aqueous sodium chloride, dried over magnesium sulfate, and filtered. Following evaporative removal of the solvent, the residue was purified by flash column chromatography (silica gel, 9:1 ethyl acetate/methanol) to give 5-3 as a tan foam.

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate, saturated aqueous sodium chloride
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customremoval of the solvent
  5. customthe residue was purified by flash column chromatography (silica gel, 9:1 ethyl acetate/methanol)

Sources & evidence

ORD record
ord-8d656532238140d1a8593b1a8c3d69d7
Source dataset
uspto-grants-2002_07
Patent number
US06413955B1

Reaction notes

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