Hydrochloric Acid → HCID 10143199, compound

HRID 1272352Notes

Reaction equation

HRID 1272352 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[C:16]([CH3:40])=[C:17]([CH3:39])[C:18]4[O:22][C:21]([CH3:24])([CH3:23])[CH:20]([O:25][CH2:26][C:27]5[CH:36]=[CH:35][C:30]([C:31]([O:33]C)=[O:32])=[CH:29][CH:28]=5)[C:19]=4[C:37]=3[CH3:38])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C1COCC1.[OH-].[Na+].Cl>CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:10][CH2:11][N:12]([C:15]3[C:16]([CH3:40])=[C:17]([CH3:39])[C:18]4[O:22][C:21]([CH3:24])([CH3:23])[CH:20]([O:25][CH2:26][C:27]5[CH:28]=[CH:29][C:30]([C:31]([OH:33])=[O:32])=[CH:35][CH:36]=5)[C:19]=4[C:37]=3[CH3:38])[CH2:13][CH2:14]2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 22935600HCID 22935600, compound

Product 1

HCID 10143199HCID 10143199, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-(((5-(4-[4-methoxyphenyl]piperazin-1-yl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-yl)oxy)methyl)benzoate (0.18 g, 0.33 mmol) obtained in Example 135 in methanol (1 mL)-THF (1 ml) was added 1N sodium hydroxide (0.5 mL). The mixture was stirred at room temperature for 16 hours. The reaction mixture was acidified with 1 N hydrochloric acid and extracted with ethyl acetate. The organic extract was washed with water and saturated aqueous sodium chloride and dried over anhydrous sodium sulfate. The residue was recrystallized from hexane-ethyl acetate to obtain 0.13 g (yield 75%) of the title compound. mp. 162–163° C.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with water and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe residue was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-97ba85b7da6b4b219fd298bbcd00c4d0
Source dataset
uspto-grants-2007_04
Patent number
US07208495B2

Reaction notes

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