Ethanol → HCID 44227315, compound

HRID 2091099Notes

Reaction equation

HRID 2091099 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]3[O:13][C:12]([CH:14]([NH:18][C:19]4[CH:24]=[CH:23][C:22]([C:25]([N:27]([CH3:35])[CH2:28][CH2:29][C:30]([O:32]CC)=[O:31])=[O:26])=[CH:21][CH:20]=4)[CH:15]([CH3:17])[CH3:16])=[C:11]([CH3:36])[C:10]=3[CH:37]=2)[CH2:3][CH2:2]1.C(O)C.[OH-].[Na+]>O1CCCC1>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]3[O:13][C:12]([CH:14]([NH:18][C:19]4[CH:20]=[CH:21][C:22]([C:25]([N:27]([CH3:35])[CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[O:26])=[CH:23][CH:24]=4)[CH:15]([CH3:17])[CH3:16])=[C:11]([CH3:36])[C:10]=3[CH:37]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 66777593HCID 66777593, compound

Product 1

HCID 44227315HCID 44227315, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of ethyl 3-[{[4-({1-[5-(cyclopropylmethoxy)-3-methyl-1-benzofuran-2-yl]-2-methylpropyl}amino)phenyl]carbonyl}(methyl)amino]propanoate (667 mg) obtained in Example A75(4) in tetrahydrofuran (3 mL) and ethanol (3 mL) was added 1N aqueous sodium hydroxide solution (2.6 mL), and the mixture was stirred at room temperature for 30 min. The reaction mixture was concentrated under reduced pressure, the residue was dissolved in water (4 mL), and 1N hydrochloric acid (2.6 mL) was added at 0° C. The mixture was stirred at 0° C. for 30 min, and the resulting precipitate was collected by filtration to give the title compound (509 mg, 81%) as a colorless amorphous form.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in water (4 mL)
  3. addition1N hydrochloric acid (2.6 mL) was added at 0° C
  4. stirringThe mixture was stirred at 0° C. for 30 min
  5. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-85fafcbf87354f32b8d91244b2056932
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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