Trifluoroacetic acid → HCID 45139976, compound

HRID 574280Notes

Reaction equation

HRID 574280 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([N:13]([CH2:30][CH2:31][CH3:32])[C:14](=[O:29])[CH2:15][N:16]3[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]3)[CH2:10]2)=[CH:5][CH:4]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([N:13]([CH2:30][CH2:31][CH3:32])[C:14](=[O:29])[CH2:15][N:16]3[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]3)[CH2:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 45139975HCID 45139975, compound

Product 1

HCID 45139976HCID 45139976, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 6a (3.87 g, 8.68 mmol) was dissolved in 40 ml of dichloromethane and 40 ml of trifluoroacetic acid was added. The mixture was stirred for overnight, at which time the solution was concentrated to dryness, dissolved in saturated NaHCO3 solution and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered, and concentrated to yield 2.91 g (97%) of 7a as yellow wax, which was used in the next reaction. 1H NMR (400 MHz, CDCl3) 0.93-0.96 (t, 3H, J=12 Hz), 1.62 (m, 3H), 1.85-1.97 (m, 3H), 2.56 (m, 1H), 2.81-2.88 (m, 5H), 2.98-3.34 (m, 9H), 3.81 (s, 3H), 6.60 (s, 1H), 6.65-6.68 (d, 1H, J=12 Hz), 6.96-6.98 (d, 1H, J=8 Hz).

Workup

  1. concentrationwas concentrated to dryness
  2. dissolutiondissolved in saturated NaHCO3 solution
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-adbbfdafd78c4ae4a15fe7ac678b94b9
Source dataset
uspto-grants-2015_05
Patent number
US09034877B2

Reaction notes

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