Trifluoroacetic acid → HCID 178497716, compound

HRID 1488069Notes

Reaction equation

HRID 1488069 reaction equation
[OH:1][C:2]1([C:6]2[N:7](COCC[Si](C)(C)C)[C:8]([C:12]3[CH:13]=[C:14]([CH:19]=[CH:20][C:21]=3[CH3:22])[C:15]([O:17][CH3:18])=[O:16])=[C:9]([CH3:11])[N:10]=2)[CH2:5][O:4][CH2:3]1.[SiH](CC)(CC)CC.FC(F)(F)C(O)=O.[OH-].[Na+]>[Cl-].[Na+].O>[OH:1][C:2]1([C:6]2[NH:7][C:8]([C:12]3[CH:13]=[C:14]([CH:19]=[CH:20][C:21]=3[CH3:22])[C:15]([O:17][CH3:18])=[O:16])=[C:9]([CH3:11])[N:10]=2)[CH2:3][O:4][CH2:5]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 14798Sodium HydroxideHCID 90030635HCID 90030635, compound2×

Product 1

HCID 178497716HCID 178497716, compound

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

Into a 100-mL round-bottom flask, was placed methyl 3-(2-(3-hydroxyoxetan-3-yl)-4-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-5-yl)-4-methylbenzoate (compound 192.4, 180 mg, 0.42 mmol), Et3SiH (1 mL) and trifluoroacetic acid (2 mL). The reaction mixture was stirred for 4 h at room temperature. The pH of the solution was adjusted to 8 with sodium hydroxide (1 M). The reaction mixture was diluted with 100 mL of brine. The aqueous phase was extracted with 2×30 mL of ethyl acetate, the combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure. This resulted in 150 mg (crude) of the title compound as an orange oil.

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. extractionThe aqueous phase was extracted with 2×30 mL of ethyl acetate
  3. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3526ed70648d49b4878fa65cb56e53cd
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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