Sodium Hydroxide → HCID 118062800, compound

HRID 920824Notes

Reaction equation

HRID 920824 reaction equation
[I:1][C:2]1[C:21]([C:22]([O:24]CC)=[O:23])=[C:5]2[CH2:6][N:7]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:8]([C:10]([F:13])([F:12])[F:11])[CH2:9][N:4]2[N:3]=1.[OH-].[Na+]>C(O)C.O>[C:17]([O:16][C:14]([N:7]1[CH:8]([C:10]([F:11])([F:12])[F:13])[CH2:9][N:4]2[N:3]=[C:2]([I:1])[C:21]([C:22]([OH:24])=[O:23])=[C:5]2[CH2:6]1)=[O:15])([CH3:20])([CH3:18])[CH3:19]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 118062365HCID 118062365, compound

Product 1

HCID 118062800HCID 118062800, compoundYield 57.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of Intermediate 346D (0.22 g, 0.450 mmol) in ethanol (2 mL) and water (2 mL) was added NaOH (0.036 g, 0.899 mmol) and the solution was stirred at RT for 16 h. The reaction mixture was concentrated under reduced pressure and the pH of the crude product was adjusted to 2 with an aqueous solution of 1.5N HCl and extracted with EtOAc (2×20 mL). The combined organic layer was dried over anhydrous Na2SO4, filtered and the filtrate concentrated under reduced pressure to afford Intermediate 346E as a white solid (0.12 g, 55%). MS(ES): m/z=462.4 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 12.4 (br, s., 1H), 5.55-5.38 (m, 1H), 5.18-5.08 (m, 1H), 4.54 (m, 3H), 1.48 (s, 9H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with EtOAc (2×20 mL)
  3. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-a77ef19266ad4f92ae213a96f5e2a079
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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