Propionic Acid → HCID 70158897, compound

HRID 2227277Notes

Reaction equation

HRID 2227277 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][C@H:8]1[CH2:12][C@@H:11]([CH3:13])[N:10]([CH2:14][C@H:15](O)[CH:16]=[CH:17][C:18]2[CH:19]=[N:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=2)[C:9]1=[O:27])([CH3:4])([CH3:3])[CH3:2].[C:29]([OH:33])(=[O:32])[CH2:30]C.[CH2:34](C(CC)(CC)C([O-])([O-])[O-])[CH3:35]>C(OCC)(=O)C>[CH2:34]([O:33][C:29](=[O:32])[CH2:30][C@@H:17]([C:18]1[CH:19]=[N:20][C:21]([O:24][CH3:25])=[CH: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:28])[C:9]1=[O:27])[CH3:35]

Participants

5

Reactant 3

HCID 1032Propionic AcidHCID 21875354TriethylorthoaceateHCID 70160912HCID 70160912, compound

Product 1

HCID 70158897HCID 70158897, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of 4-5 (400 mg) and propionic acid (5 mg) in triethylorthoacetate (5 mL) was heated at 130° C. for 2 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, 7:3 ethyl acetate/hexanes) to give 4-6 as a colorless oil.

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, 7:3 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-0cd3a7b2fc1e40e89b6aba5fda451499
Source dataset
uspto-grants-2002_07
Patent number
US06413955B1

Reaction notes

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