Trifluoroacetic acid → HCID 76684443, compound

HRID 925211Notes

Reaction equation

HRID 925211 reaction equation
C(OC([N:8]1[CH2:32][CH2:31][C:12]2[C:13]3[C:14](O)([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[O:28][CH3:29])[C:15]([F:21])([F:20])[CH2:16][C:17]=3[CH:18]=[CH:19][C:11]=2[CH2:10][CH2:9]1)=O)(C)(C)C.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:21][C:15]1([F:20])[CH:14]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[O:28][CH3:29])[C:13]2[C:12]3[CH2:31][CH2:32][NH:8][CH2:9][CH2:10][C:11]=3[CH:19]=[CH:18][C:17]=2[CH2:16]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 12052Triethylsilane2×HCID 86725324HCID 86725324, compound

Product 1

HCID 76684443HCID 76684443, compoundYield 62.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a glass vial, the product from step (c) (112 mg, 0.251 mmol) dissolved in 2 ml DCM was added. To this stirred solution, triethylsilane (603 μL, 3.77 mmol) was added, followed by TFA (290 μL, 3.77 mmol). After stirring at room temperature for 16 hours, additional triethylsilane (603 μL, 3.77 mmol) and TFA (290 μL, 3.77 mmol) were added. The reaction mixture was stirred for an additional 16 hours. The volatiles were then evaporated in vacuo and the residue diluted with 2M HCl (20 ml). The aqueous mixture was washed with diethyl ether (2×), basified with 2M NaOH to pH 10, and extracted with DCM (3×). The combined DCM extracts were washed with brine, dried over Na2SO4, and solvent evaporated in vacuo to give the title compound as a white semi-solid (52 mg). 1H NMR (300 MHz, CDCl3) δ 7.23-7.20 (m, 1H); 7.08-7.02 (m, 2H); 6.95-6.91 (m, 1H); 6.78 (t, J=7.5 Hz, 1H); 6.51 (bs, 1H); 5.15 (d, J=21.0 Hz, 1H); 3.91 (s, 3H); 3.47-3.28 (m, 2H); 2.97-2.81 (m, 4H); 2.72-2.62 (m, 2H); 2.51-2.46 (2H); 1.68 (bs, 1H); MS: ESI (positive): 330 (M+1).

Workup

  1. additionwas added
  2. stirringThe reaction mixture was stirred for an additional 16 hours
  3. customThe volatiles were then evaporated in vacuo
  4. additionthe residue diluted with 2M HCl (20 ml)
  5. washThe aqueous mixture was washed with diethyl ether (2×)
  6. extractionextracted with DCM (3×)
  7. washThe combined DCM extracts were washed with brine
  8. dry with materialdried over Na2SO4, and solvent
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-9f7483518f814e6f8bbb39d204de9130
Source dataset
uspto-grants-2016_03
Patent number
US09284277B2

Reaction notes

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