Ammonia → HCID 90202338, compound

HRID 929761Notes

Reaction equation

HRID 929761 reaction equation
C([O:3][C:4]([C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])=[CH:13][CH:12]=2)[CH:7]=1)=O)C.[NH3:25]>CCO>[C:21]([Si:18]([CH3:20])([CH3:19])[O:17][C:14]1[CH:15]=[CH:16][C:11]([C:8]2[CH:7]=[C:6]([C:4]([NH2:25])=[O:3])[O:10][N:9]=2)=[CH:12][CH:13]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 90202312HCID 90202312, compound2×

Product 1

HCID 90202338HCID 90202338, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-isoxazole-5-carboxylic acid ethyl ester (which may be prepared as described in Preparation of Intermediate 12; 500 mg, 1.4 mmol) was dissolved in a saturated solution of NH3 in EtOH (200 mL). The mixture was stirred at room temperature for 60 h. The solvent was evaporated and the residue was purified by chromatography (50-60% EtOAc/hexanes) to give 3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-isoxazole-5-carboxylic acid amide (160 mg, 35%) as a white solid.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by chromatography (50-60% EtOAc/hexanes)

Sources & evidence

ORD record
ord-4e2067b3cda24e679e0448a4335c9b96
Source dataset
uspto-grants-2016_03
Patent number
US09296711B2

Reaction notes

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