Sodium Hydroxide → HCID 11845472, compound

HRID 1366920Notes

Reaction equation

HRID 1366920 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[NH:9][CH:10]=[C:11]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Br:21])[CH:12]=1)=[O:7])C>CO>[Br:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH2:14][CH2:13][C:11]1[CH:12]=[C:8]([C:6]([OH:7])=[O:5])[NH:9][CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57435099HCID 57435099, compound

Product 1

HCID 11845472HCID 11845472, compoundYield 51.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Freshly prepared aq. NaOH (10 M in H2O, 13.04 mmol) was added to a stirring, room temperature solution of 64 (0.8402 g, 2.608 mmol) in MeOH (6.5 mL, 0.4 M) under N2. The reaction was heated to reflux until the reaction was judged complete by HPLC (10 min): The product was concentrated and then dissolved in 10 mL H2O. The product was extracted with EtOAc until the organic layer no longer turned yellow, then the aqueous layer was made acidic (pH=2) with the dropwise addition of 10% aq. HCl. The product oiled out of solution, so EtOAc was added, and the organic layer was removed, dried with Na2SO4, filter, concentrated to obtain 65 (0.3934 g, 51.3%) as a white solid (Note: An undesired impurity has a retention time of 11.066 min by HPLC): 1H (CD3OD, 400 MHz): δ 7.51 (1H, d, J=7.8 Hz), 7.24-7.16 (2H, m), 7.05 (1H, ddd, J=8.2, 6.3, 2.9 Hz), 6.72 (1H, s), 6.71 (1H, s), 2.96 (2H, t, J=8.0 Hz), 2.73 (2H, t, J=7.8 Hz)) ppm. 13C (CD3OD, 100 MHz): δ 164.48, 142.42, 133.71, 131.80, 128.79, 128.53, 125.89, 125.20, 123.54, 122.61, 116.38, 38.99, 28.20 ppm. DEPT (CDCl3, 100 MHz): CH2 carbons: 38.99, 28.20; CH carbons: 133.71, 131.80, 128.79, 128.53, 122.61, 116.38 ppm. HPLC: 10.035 min.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux until the reaction
  3. customwas judged complete by HPLC (10 min)
  4. concentrationThe product was concentrated
  5. dissolutiondissolved in 10 mL H2O
  6. extractionThe product was extracted with EtOAc until the organic layer no longer turned yellow
  7. additionwith the dropwise addition of 10% aq. HCl
  8. additionwas added
  9. customthe organic layer was removed
  10. dry with materialdried with Na2SO4
  11. filtrationfilter
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-b71b02eeddfc49598f7003a171e166e3
Source dataset
uspto-grants-2011_02
Patent number
US07893098B2

Reaction notes

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