Sodium Hydroxide → HCID 66779124, compound

HRID 2091402Notes

Reaction equation

HRID 2091402 reaction equation
[CH:1]1([CH:6]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]([NH:27][CH2:28][CH2:29][C:30]([O:32]CC)=[O:31])=[O:26])=[CH:21][CH:20]=2)[C:7]2[O:8][C:9]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:10]=3[C:11]=2[CH3:12])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C.O1CCCC1>[CH:1]1([CH:6]([NH:18][C:19]2[CH:20]=[CH:21][C:22]([C:25]([NH:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[O:26])=[CH:23][CH:24]=2)[C:7]2[O:8][C:9]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:10]=3[C:11]=2[CH3:12])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66778678HCID 66778678, compound

Product 1

HCID 66779124HCID 66779124, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 3-{[(4-{[cyclopentyl(5-fluoro-3-methyl-1-benzofuran-2-yl)methyl]amino}phenyl)carbonyl]amino}propanoate (363 mg) synthesized in Example A189 was dissolved in ethanol (1.5 mL) and tetrahydrofuran (1.5 mL), 1N aqueous sodium hydroxide solution (1.5 mL) was added to the solution, and the mixture was stirred at room temperature for 30 min. The solvent was evaporated under reduced pressure, water (4 mL) was added to the mixture, and the mixture was neutralized with 1N hydrochloric acid under ice-cooling, and the mixture was stirred for 30 min. The resulting precipitate was collected by filtration, and dried to give the title compound (283 mg, 83%) as a colorless solid.

Workup

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

Sources & evidence

ORD record
ord-c396401dc976446f89450845c3a29dc2
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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