Potassium trimethylsilanolate → HCID 59581298, compound

HRID 386608Notes

Reaction equation

HRID 386608 reaction equation
C[O:2][C:3](=[O:22])[CH2:4][N:5]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[C:9]([F:14])[CH:8]=1.C[Si](C)(C)[O-].[K+]>C1COCC1.CCOC(C)=O>[C:18]([O:17][C:15]([N:5]([CH2:4][C:3]([OH:22])=[O:2])[CH2:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[C:9]([F:14])[CH:8]=1)=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 2

HCID 23668039Potassium trimethylsilanolateHCID 59581297HCID 59581297, compound

Product 1

HCID 59581298HCID 59581298, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of methyl[(tert-butoxycarbonyl)(3,5-difluorobenzyl)amino]acetate from Step B (1.89 g, 5.99 mmol) in THF (60 mL) was added potassium trimethylsilanolate (1.00 g, 7.79 mmol). The reaction mixture was allowed to stir at ambient temperature for 72 hours. The bulk of the THF was then removed in vacuo, and the residue was diluted with water. The aqueous layer was extracted three times with diethyl ether, discarding ether extracts. The aqueous layer was placed under reduce pressure to remove residual ether and then was brought to an acidic pH with aqueous 1 M HCl to obtain an oil. The oil was dissolved in EtOAc and the combined organics were dried over sodium sulfate, filtered and concentrated in vacuo to yield the title compound. MS: m/z=319 (M+18 (NH4+)).

Workup

  1. customThe bulk of the THF was then removed in vacuo
  2. additionthe residue was diluted with water
  3. extractionThe aqueous layer was extracted three times with diethyl ether
  4. customto remove residual ether
  5. customto obtain an oil
  6. dry with materialthe combined organics were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-03244306c13545b8b9612fd910553dc0
Source dataset
uspto-grants-2013_02
Patent number
US08372859B2

Reaction notes

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