Sodium Hydroxide → HCID 11513041, compound

HRID 551946Notes

Reaction equation

HRID 551946 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH:36]=[CH:35][C:13]([CH2:14][N:15]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:16]3[CH:28]=[CH:27][C:19]4[O:20]C(C)(C)[O:22][C:23](=[O:24])[C:18]=4[CH:17]=3)=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[C:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:14][N:15]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:16]3[CH:28]=[CH:27][C:19]([OH:20])=[C:18]([CH:17]=3)[C:23]([OH:24])=[O:22])=[CH:35][CH:36]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57554566HCID 57554566, compound

Product 1

HCID 11513041HCID 11513041, compoundYield 29.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-({4-[(4-chlorophenyl)ethynyl]benzyl}(hexyl)amino)-2,2-dimethyl-4H-1,3-benzodioxin-4-one (3.40 g, 6.77 mmol) in MeOH (150 mL) was added an aqueous solution of NaOH (5.5 mL, 5N). The reaction mixture was stirred at rt for 1.5 hr and a solid precipitated out. Water (250 mL) was added, and then the precipitate was filtered and washed with water (3×). The solid was taken up with MeOH (150 mL), an aqueous solution of NaOH (5.5 mL, 5N) was added and the resulting mixture was heated at 60° C. for 15 hrs. Then an aqueous solution of HCl (10 mL, 5N) and water (400 mL) were added and the mixture was extracted with Et2O (500+2×250 mL). The combined organic layers were dried over MgSO4 and evaporated under reduced pressure. Purification by crystallization (acetone/water) gave 909 mg (29%) of the title compound as a white powder. HPLC, Rt: 4.5 min (purity: 99.5%). LC/MS, M+(ESI): 462.0, M−(ESI): 459.9. 1H NMR (CDCl3) δ: 7.55 (d, J=8.3 Hz, 2H), 7.48 (m, 4H), 7.26 (d, J=7.9 Hz, 2H), 7.00 (d, J=2.8 Hz, 1H), 6.96 (dd, J=9.0, 2.8 Hz, 1H), 6.78 (d, J=9.0 Hz, 1H), 4.47 (s, 2H), 3.30 (m, 2H), 1.51 (m, 2H), 1.24 (m, 6H), 0.83 (m, 3H).

Workup

  1. customa solid precipitated out
  2. additionWater (250 mL) was added
  3. filtrationthe precipitate was filtered
  4. washwashed with water (3×)
  5. additionan aqueous solution of NaOH (5.5 mL, 5N) was added
  6. temperaturethe resulting mixture was heated at 60° C. for 15 hrs
  7. additionThen an aqueous solution of HCl (10 mL, 5N) and water (400 mL) were added
  8. extractionthe mixture was extracted with Et2O (500+2×250 mL)
  9. dry with materialThe combined organic layers were dried over MgSO4
  10. customevaporated under reduced pressure
  11. customPurification
  12. customby crystallization (acetone/water)

Sources & evidence

ORD record
ord-9f48c46aa85e448bb7f1e824ee6b3e51
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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