Sodium Hydroxide → HCID 70913732, compound

HRID 1844752Notes

Reaction equation

HRID 1844752 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[N:20]([CH2:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[C:19]([CH3:28])=[C:18]([S:29]([NH2:32])(=[O:31])=[O:30])[CH:17]=2)[CH:8]=[C:9]([C:11]([C:14]#[N:15])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[OH-:33].[Na+]>CCO.O>[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:13])([CH3:12])[C:14]([NH2:15])=[O:33])[CH:8]=[C:7]([C:16]2[N:20]([CH2:21][CH:22]3[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]3)[C:19]([CH3:28])=[C:18]([S:29](=[O:31])(=[O:30])[NH2:32])[CH:17]=2)[CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66562431HCID 66562431, compound

Product 1

HCID 70913732HCID 70913732, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of compound 45 (455 mg, 1.0 mmol) and NaOH (3.2 g, 80 mmol) in EtOH (10 mL) and water (10 mL) was stirred at reflux overnight, cooled to rt, concentrated and redissolved in H2O (30 mL), acidified with 1N HCl solution to pH=6. The formed solid was collected by filtration, washed with water and dried under vacuum. The residue was purified by CC (DCM/MeOH=50/1) to give compound 47 (400 mg, 85%) of as a white solid.

Workup

  1. temperatureat reflux overnight
  2. concentrationconcentrated
  3. dissolutionredissolved in H2O (30 mL)
  4. filtrationThe formed solid was collected by filtration
  5. washwashed with water
  6. customdried under vacuum
  7. customThe residue was purified by CC (DCM/MeOH=50/1)

Sources & evidence

ORD record
ord-3e3f5ffbf90e400cb33c9bb67f63b272
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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