Trifluoroacetic acid → HCID 19047660, compound

HRID 1780811Notes

Reaction equation

HRID 1780811 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][C:10]([C:12]1[C:13]2[CH:14]=[CH:15][NH:16][C:17]=2[CH:18]=[CH:19][CH:20]=1)=[O:11].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>CCCCCC.C(OCC)(=O)C>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][C:10]([C:12]1[C:13]2[CH2:14][CH2:15][NH:16][C:17]=2[CH:18]=[CH:19][CH:20]=1)=[O:11]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 19047753HCID 19047753, compound

Product 1

HCID 19047660HCID 19047660, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

To compound 11 (0.15 g) was added triethylsilane (0.36 mL) and trifluoroacetic acid (10 mL). After stirring for 10 min. the solution was concentrated in vacuo and the residue was partitioned between ethyl acetate and sodium bicarbonate. The ethyl acetate layer was washed with saturated sodium chloride, dried over magnesium sulfate and concentrated in vacuo to afford the crude product. Trituration with hexane/ethyl acetate 8/2 gave the product. NMR (300 MHz, CDCl3) δ 7.62 (1H, d, J=3 Hz), 7.53 (1H, s), 7.13 (2H, q, J=3 Hz), 7.04 (2H, m), 6.77 (1H, d, J=3 Hz), 3.62 (2H, t, J=3 Hz), 3.39 (2H, t, J=3 Hz), 2.33 (3H, s), 2.21 (3H, s).

Workup

  1. concentrationwas concentrated in vacuo
  2. customthe residue was partitioned between ethyl acetate and sodium bicarbonate
  3. washThe ethyl acetate layer was washed with saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto afford the crude product

Sources & evidence

ORD record
ord-f79586e1b6e14be78fabcca5a515245a
Source dataset
uspto-grants-1997_05
Patent number
US05631280

Reaction notes

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