Hydrochloric Acid → HCID 58047306, compound

HRID 1888768Notes

Reaction equation

HRID 1888768 reaction equation
[O:1]=[C:2]([NH:9][CH:10]([C:12]1[O:13][C:14]2[CH:20]=[C:19]([CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][CH3:32])=[CH:25][CH:24]=3)[CH:18]=[CH:17][C:15]=2[CH:16]=1)[CH3:11])[CH2:3][C:4]([O:6]CC)=[O:5].[OH-].[Na+].Cl>C1COCC1.CO>[O:1]=[C:2]([NH:9][CH:10]([C:12]1[O:13][C:14]2[CH:20]=[C:19]([CH2:21][CH2:22][C:23]3[CH:24]=[CH:25][C:26]([O:29][CH2:30][CH2:31][CH3:32])=[CH:27][CH:28]=3)[CH:18]=[CH:17][C:15]=2[CH:16]=1)[CH3:11])[CH2:3][C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58047317HCID 58047317, compound

Product 1

HCID 58047306HCID 58047306, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-oxo-3-[(1-{6-[2-(4-propoxyphenyl)ethyl]-1-benzofuran-2-yl}ethyl)amino]propanoate (214 mg, 0.489 mmol) obtained in Example 34 in THF-methanol (5 mL-3 mL) was added 1N aqueous sodium hydroxide solution (0.750 mL, 0.750 mmol), and the mixture was stirred at room temperature for 15 min. The reaction mixture was acidified with 1N hydrochloric acid and extracted twice with ethyl acetate, and the combined organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was washed with diethyl ether to give the title compound (158 mg, yield 79%) as a white solid.

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialthe combined organic layer was dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated
  4. washthe residue was washed with diethyl ether

Sources & evidence

ORD record
ord-6208c56ab4b94f5689346b481af6bf71
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

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