Acetic Acid → HCID 68519399, compound

HRID 1863967Notes

Reaction equation

HRID 1863967 reaction equation
C([O:5][C:6](=O)[NH:7][C@H:8]([CH2:24][C:25]1[CH:30]=[C:29]([F:31])[C:28]([F:32])=[CH:27][C:26]=1[F:33])[CH2:9][C:10]([NH:12][NH:13][C:14]1[N:19]2[N:20]=[C:21]([CH3:23])[N:22]=[C:18]2[CH2:17][CH2:16][N:15]=1)=O)(C)(C)C.[C:35](O)(=O)C>>[CH3:23][C:21]1[N:22]=[C:18]2[N:19]([C:14]3[N:15]([C:10]([CH2:9][C@H:8]([NH:7][C:6](=[O:5])[CH3:35])[CH2:24][C:25]4[CH:30]=[C:29]([F:31])[C:28]([F:32])=[CH:27][C:26]=4[F:33])=[N:12][N:13]=3)[CH2:16][CH2:17]2)[N:20]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 91285248HCID 91285248, compound

Product 1

HCID 68519399HCID 68519399, compound

Procedure

The crude residue from Step A was dissolved in 5 mL of glacial acetic acid, and the resulting solution was stirred at reflux for 60 h. The cooled solution was concentrated, and the residue was partitioned between 1:1 ethyl acetate:tetrahydrofuran and saturated sodium carbonate aqueous solution. The organic phase was dried over magnesium sulfate, filtered, and concentrated to dryness. Purification of the residue by preparative thin-layer chromatography on silica gel (three successive developments in 95:5, 92.5:7.5, and 90:10 dichloromethane:methanol) afforded the title compound as a stiff foam. LC-MS 406 (M+1).

Workup

  1. temperatureat reflux for 60 h
  2. concentrationThe cooled solution was concentrated
  3. customthe residue was partitioned between 1:1 ethyl acetate
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customPurification of the residue by preparative thin-layer chromatography on silica gel (three successive developments in 95:5, 92.5:7.5, and 90:10 dichloromethane:methanol)

Sources & evidence

ORD record
ord-a28e512b1db448588f28f61238f0d71d
Source dataset
uspto-grants-2009_12
Patent number
US07625888B2

Reaction notes

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