Sodium Bicarbonate → HCID 86712311, compound

HRID 592429Notes

Reaction equation

HRID 592429 reaction equation
[CH3:1][C:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]#[C:14][Si](CC)(CC)CC)([CH3:6])[C:3]([NH2:5])=[O:4].CCCC[N+](CCCC)(CCCC)CCCC.[F-].C([O-])(O)=O.[Na+]>C1COCC1>[C:13]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:2]([CH3:6])([CH3:1])[C:3]([NH2:5])=[O:4])#[CH:14]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 86712310HCID 86712310, compound

Product 1

HCID 86712311HCID 86712311, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-methyl-2-(2-((triethylsilyl)ethynyl)phenyl)propanamide A35 (0.116 g, 0.385 mmol) in THF (5 mL) was stirred with TBAF (1.0 M in THF, 0.40 mL, 0.40 mmol) at 0° C. for 2 minutes. Sat. aq. NaHCO3 (20 mL) was added and the aqueous phase was extracted with EtOAc (3×30 mL). The combined organics were washed with brine, dried (MgSO4) and the solvent was removed in vacuo. The resultant yellow oil was purified by column chromatography (Biotage Isolera, 24 g SiO2 cartridge, 20-100% EtOAc in petroleum benzine 40-60° C.) to give the title compound A36 as a yellow solid (0.060 g, 83%). LCMS-D: rt 3.02 min; m/z 188 [M+H]+.

Workup

  1. extractionthe aqueous phase was extracted with EtOAc (3×30 mL)
  2. washThe combined organics were washed with brine
  3. dry with materialdried (MgSO4)
  4. customthe solvent was removed in vacuo
  5. customThe resultant yellow oil was purified by column chromatography (Biotage Isolera, 24 g SiO2 cartridge, 20-100% EtOAc in petroleum benzine 40-60° C.)

Sources & evidence

ORD record
ord-0c036c05f59f49a99e371e6ed30aa40b
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

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