Potassium Hydroxide → HCID 66977055, compound

HRID 2363796Notes

Reaction equation

HRID 2363796 reaction equation
CN(C)C(=O)[O:4][C:5]1[C:14]([C:15]2[C:16]([O:26]C(=O)N(C)C)=[CH:17][CH:18]=[C:19]3[C:24]=2[N:23]([CH3:25])[CH2:22][CH2:21][CH2:20]3)=[C:13]2[C:8]([CH2:9][CH2:10][CH2:11][N:12]2[CH3:32])=[CH:7][CH:6]=1.[OH-].[K+]>>[CH3:25][N:23]1[C:24]2[C:19](=[CH:18][CH:17]=[C:16]([OH:26])[C:15]=2[C:14]2[C:5]([OH:4])=[CH:6][CH:7]=[C:8]3[C:13]=2[N:12]([CH3:32])[CH2:11][CH2:10][CH2:9]3)[CH2:20][CH2:21][CH2:22]1

Participants

3

Reactant 2

HCID 14797Potassium HydroxideHCID 66977231HCID 66977231, compound

Product 1

HCID 66977055HCID 66977055, compoundYield 78.3%

Procedure

A solution of 6 (2.0 g, 4.29 mmol) in 10 wt. % methanolic KOH (45 mL) was stirred at reflux for 20 h. The resulting solution was allowed to cool to room temperature and concentrated in vacuo. The residue was dissolved in H2O and the pH adjusted to a value of 7 by careful addition of 1 M aq. HCl. The aqueous phase was saturated with NaCl and extracted with EtOAc (50 mL×6). The combined organic extracts were washed with brine, dried over anhydrous magnesium sulfate, filtered and, concentrated in vacuo. The residue was further purified by column chromatography (eluting with EtOAc/Hexane=4:1) to yield 7 (1.09 g, 76%) as a white solid.

Workup

  1. temperatureat reflux for 20 h
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in H2O
  4. additionthe pH adjusted to a value of 7 by careful addition of 1 M aq. HCl
  5. extractionextracted with EtOAc (50 mL×6)
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was further purified by column chromatography (eluting with EtOAc/Hexane=4:1)

Sources & evidence

ORD record
ord-44d7652872e84fc7aa9e2a14295aac9b
Source dataset
uspto-grants-2014_04
Patent number
US08691992B2

Reaction notes

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