Trifluoroacetic acid → HCID 68109011, compound

HRID 404573Notes

Reaction equation

HRID 404573 reaction equation
C(O)(C(F)(F)F)=O.[CH3:8][N:9]([CH2:11][C:12]1[CH:13]=[C:14]([NH:22]C(=O)OC(C)(C)C)[CH:15]=[CH:16][C:17]=1[Si:18]([CH3:21])([CH3:20])[CH3:19])[CH3:10].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:10][N:9]([CH2:11][C:12]1[CH:13]=[C:14]([CH:15]=[CH:16][C:17]=1[Si:18]([CH3:20])([CH3:19])[CH3:21])[NH2:22])[CH3:8]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 68109870HCID 68109870, compound2×

Product 1

HCID 68109011HCID 68109011, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 0° C., 5 ml TFA was slowly added into a solution of tert-butyl 3-((dimethylamino)methyl)-4-(trimethylsilyl)phenylcarbamate (compound 29) in CH2Cl2. The reaction mixture was stirred at 0° for 2 hours. After adjusted with saturated NaHCO3 solution to pH 8, the reaction mixture was extracted by ethyl acetate. The organic layer was dried and evaporated to give a crude product, which was purified using column chromatography to give the product. (0.9 g, 32%)

Workup

  1. extractionthe reaction mixture was extracted by ethyl acetate
  2. customThe organic layer was dried
  3. customevaporated

Sources & evidence

ORD record
ord-7335150560ed46e695757e382708a605
Source dataset
uspto-grants-2014_06
Patent number
US08748610B2

Reaction notes

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