Sodium Hydroxide → HCID 66778972, compound

HRID 2091414Notes

Reaction equation

HRID 2091414 reaction equation
[CH3:1][N:2]([C:10]([C:12]1[CH:17]=[CH:16][C:15]([NH:18][CH:19]([C:23]2[O:24][C:25]3[CH:32]=[CH:31][C:30]([O:33][CH:34]4[CH2:39][CH2:38][S:37][CH2:36][CH2:35]4)=[CH:29][C:26]=3[C:27]=2[CH3:28])[CH:20]([CH3:22])[CH3:21])=[CH:14][CH:13]=1)=[O:11])[CH2:3][CH2:4][C:5]([O:7]CC)=[O:6].[OH-].[Na+]>C(O)C.O1CCCC1>[CH3:1][N:2]([C:10]([C:12]1[CH:13]=[CH:14][C:15]([NH:18][CH:19]([C:23]2[O:24][C:25]3[CH:32]=[CH:31][C:30]([O:33][CH:34]4[CH2:35][CH2:36][S:37][CH2:38][CH2:39]4)=[CH:29][C:26]=3[C:27]=2[CH3:28])[CH:20]([CH3:22])[CH3:21])=[CH:16][CH:17]=1)=[O:11])[CH2:3][CH2:4][C:5]([OH:7])=[O:6]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66777859HCID 66777859, compound

Product 1

HCID 66778972HCID 66778972, compoundYield 91.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 3-(methyl{[4-({2-methyl-1-[3-methyl-5-(tetrahydro-2H-thiopyran-4-yloxy)-1-benzofuran-2-yl]propyl}amino)phenyl]carbonyl}amino)propanoate (485 mg) synthesized in Example A203 was dissolved in ethanol (2.0 mL) and tetrahydrofuran (2.0 mL), and 1N aqueous sodium hydroxide solution (1.96 mL) was added to the solution, and the mixture was stirred at room temperature for 0.5 hr. The solvent was evaporated under reduced pressure, water (4 mL) was added to the residue, and the mixture was neutralized with 1N hydrochloric acid (1.96 mL) under ice-cooling, and stirred for 30 min. The resulting precipitate was collected by filtration, and dried to give the title compound (421 mg, 91%) as a colorless amorphous form.

Workup

  1. customThe solvent was evaporated under reduced pressure, water (4 mL)
  2. additionwas added to the residue
  3. temperaturecooling
  4. stirringstirred for 30 min
  5. filtrationThe resulting precipitate was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-da4bc54e228a4f49b2781aa26e4590f1
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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