Sodium Hydroxide → HCID 118062266, compound

HRID 920796Notes

Reaction equation

HRID 920796 reaction equation
[F:1][C:2]1([F:16])[CH2:5][C:4]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)([C:6]([O:8]C)=[O:7])[CH2:3]1.[OH-].[Na+]>C1COCC1.O>[F:16][C:2]1([F:1])[CH2:5][C:4]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)([C:6]([OH:8])=[O:7])[CH2:3]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 118062001HCID 118062001, compound

Product 1

HCID 118062266HCID 118062266, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Intermediate 311D (250 mg, 1.100 mmol) in THF (2 mL) and water (1 mL) was added NaOH (132 mg, 3.30 mmol) and the reaction mixture was stirred at RT for 12 h. The reaction mixture was concentrated; the pH of the residue was adjusted to 2 with a 1.5N aq. solution of HCl and extracted with EtOAc (3×15 mL). The combined organic layer was dried over Na2SO4, filtered and concentrated to afford Intermediate 311E as a colorless semi-solid (160 mg, 68% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.35 (br. s., 1H), 8.65-8.54 (m, 1H), 8.53-8.46 (m, 1H), 7.83-7.74 (m, 1H), 7.46-7.35 (m, 1H), 3.47-3.35 (m, 2H), 3.23-3.08 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with EtOAc (3×15 mL)
  3. dry with materialThe combined organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-342617432fbc48c5a18bcc3f232d376e
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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