Hydrochloric Acid → HCID 11678695, compound

HRID 551909Notes

Reaction equation

HRID 551909 reaction equation
[C:1]([C:5]1[CH:44]=[CH:43][C:8]([CH2:9][N:10]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]#[C:32][C:33]3[CH:38]=[CH:37][C:36]([CH2:39][CH2:40][CH2:41][CH3:42])=[CH:35][CH:34]=3)=[CH:27][CH:26]=2)[C:11]2[CH:23]=[CH:22][C:14]3[O:15]C(C)(C)[O:17][C:18](=[O:19])[C:13]=3[CH:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].O[Li].O.[ClH:48].[Na+].[Cl-]>O1CCOCC1.O>[ClH:48].[C:1]([C:5]1[CH:44]=[CH:43][C:8]([CH2:9][N:10]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]#[C:32][C:33]3[CH:38]=[CH:37][C:36]([CH2:39][CH2:40][CH2:41][CH3:42])=[CH:35][CH:34]=3)=[CH:27][CH:26]=2)[C:11]2[CH:23]=[CH:22][C:14]([OH:15])=[C:13]([CH:12]=2)[C:18]([OH:19])=[O:17])=[CH:7][CH:6]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 168937Lithium hydroxide, monohydrateHCID 11585104HCID 11585104, compound

Product 1

HCID 11678695HCID 11678695, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of 6-((4-tert-butylbenzyl){4-[(4-butylphenyl)ethynyl]benzyl}amino)-2,2-dimethyl-4H-1,3-benzodioxin-4-one (71 mg, 0.12 mmol) in dioxane (2 ml) was added a solution of LiOH hydrate (25 mg, 0.60 mmol) in water (0.2 mL). The reaction mixture was heated at 80° C. for 3 hrs. Then a solution of HCl in dioxane (1 mL, 4N) and a saturated aqueous solution of NaCl (5 mL) were added and extracted with Et2O (2×10 mL). The combined organic layers were dried over Na2SO4 and the solvents were removed under reduced pressure. The residue was dissolved in a solution of HCl in Et2O (1 mL, 1N) and DCM (1 mL). Evaporation of the solvent under reduced pressure gave 57 mg (64%) of the title compound as a beige solid. HPLC, Rt: 5.7 min (purity: 79.0%). 1H NMR (CDCl3) δ: 8.08-6.85 (m, 15H), 4.69 (brs, 4H), 2.61 (t, J=7.7 Hz, 2H), 1.59 (m, 2H), 1.34 (m, 2H), 1.24 (s, 9H), 0.93 (t, J=7.3 Hz, 3H).

Workup

  1. extractionextracted with Et2O (2×10 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. customthe solvents were removed under reduced pressure
  4. dissolutionThe residue was dissolved in a solution of HCl in Et2O (1 mL, 1N) and DCM (1 mL)
  5. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-a31e96a8601246d8bbe91f9d63f25bba
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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