Trifluoroacetic acid → HCID 45139976, compound

HRID 574297Notes

Reaction equation

HRID 574297 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15](=[O:32])[N:16]([CH:20]2[CH2:29][CH2:28][C:27]3[C:22](=[CH:23][C:24]([O:30][CH3:31])=[CH:25][CH:26]=3)[CH2:21]2)[CH2:17][CH2:18][CH3:19])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:31][O:30][C:24]1[CH:23]=[C:22]2[C:27]([CH2:28][CH2:29][CH:20]([N:16]([CH2:17][CH2:18][CH3:19])[C:15](=[O:32])[CH2:14][N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[CH2:21]2)=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 45139975HCID 45139975, compound

Product 1

HCID 45139976HCID 45139976, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 36a (5.1 g, 11.5 mmol) was dissolved in 40 ml of dichloromethane and 40 ml of trifluoroacetic acid was added. The mixture was stirred for 3 hr, at which time the solution was concentrated to dryness, dissolved in sat. NaHCO3, and extracted with EtOAc. The organic layer was dried (Na2SO4), filtered, and concentrated to yield 3.8 g (96%) of 37a, which was used as is in the next reaction. 1H NMR (400 MHz, CDCl3) 0.93-0.96 (t, 3H, J=7.6 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), 6.60-6.61 (dd, 1H, J=1.6 Hz), 6.65-6.78 (m, 1H), 6.95-6.98 (d, 1H, J=8.8 Hz).

Workup

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

Sources & evidence

ORD record
ord-ba9003a8bac64cf08a97e9d034992738
Source dataset
uspto-grants-2015_05
Patent number
US09034877B2

Reaction notes

Loading…