Hydrochloric Acid → HCID 69215906, compound

HRID 272688Notes

Reaction equation

HRID 272688 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:10]=[CH:11][C:12]3[C:18](=[O:19])[NH:17][C:16]4[CH:20]=[C:21]([C:24]([CH3:30])([CH3:29])[C:25]([O:27]C)=[O:26])[CH:22]=[CH:23][C:15]=4[NH:14][C:13]=3[CH:31]=2)[CH:5]=[C:4]([F:32])[N:3]=1.[Li+].[OH-].Cl>C1COCC1.O>[F:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:10]=[CH:11][C:12]3[C:18](=[O:19])[NH:17][C:16]4[CH:20]=[C:21]([C:24]([CH3:30])([CH3:29])[C:25]([OH:27])=[O:26])[CH:22]=[CH:23][C:15]=4[NH:14][C:13]=3[CH:31]=2)[CH:5]=[C:4]([F:32])[N:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 69220175HCID 69220175, compound

Product 1

HCID 69215906HCID 69215906, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Example 205A (0.52 g, 1.18 mmol) and LiOH (0.144 g, 6.0 mmol) in 20 mL of THF and 20 mL of H2O was heated under reflux overnight. After the solution cooled to room temperature, the solution was neutralized with 10% HCl, and extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4), filtrated and concentrated under vacuum to give the title compound. MS (DCI) m/e 425 (M+H)+; 1H NMR (500 MHz, DMSO-d6) δ 12.27 (br, 1H), 9.72 (s, 1H), 9.68 (s, 1H), 7.98 (s, 1H), 7.75 (d, J=8.73 Hz, 1H), 7.06 (s, 1H), 6.96-6.99 (m, 3H), 6.74 (dd, J=8.73, 2.18 Hz, 1H), 6.62 (s, 2H), 1.46 (s, 6H).

Workup

  1. temperatureunder reflux overnight
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltrated
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f601ec3ef0ab4e9ebdcea11a64616640
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

Loading…