Trifluoroacetic acid → HCID 9925055, compound

HRID 1860664Notes

Reaction equation

HRID 1860664 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:19][C:20]([CH3:28])([CH3:27])[CH2:21][C:22]([O:24]CC)=[O:23])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1.FC(F)(F)C(O)=O>CO.[OH-].[Na+]>[F:1][C:2]1[CH:3]=[C:4]([CH2:19][C:20]([CH3:28])([CH3:27])[CH2:21][C:22]([OH:24])=[O:23])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 12018739HCID 12018739, compound

Product 1

HCID 9925055HCID 9925055, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

The product of STEP 8 (370 mg, 0.95 mmol) was dissolved in 20 ml methanol and 20 ml 1N sodium hydroxide solution . The reaction was stirred at room temperature for 16 h, and acidified with trifluoroacetic acid (3 ml). Solvents were evaporated and residue was purified on HPLC using acetonitrile gradient 10-50% in 30 min to yield 300 mg. FAB-MS: (MH+)=361. H NMR(CDCl3) δ1.03 (s, 6H), 2.20 (s, 2H), 2.22 (p, 2H), 2.62 (s, 2IH), 3.58 (q, 2H), 4.14 (t, 2H), 6.72 (t, 1H), 6.86-6.98 (m, 4H), 7.70 (m, 2H); Anal. Calcd. for C20H25N2O3F plus 1.4 CF3COOH: C, 52.66; H, 5.12; N, 5.39. Found: C, 52.56; H, 5.23; N, 5.09.

Workup

  1. customSolvents were evaporated
  2. customresidue was purified on HPLC
  3. customin 30 min
  4. customto yield 300 mg

Sources & evidence

ORD record
ord-829a565abf474c84a8602a7f624b9cf3
Source dataset
uspto-grants-2003_03
Patent number
US06531494B1

Reaction notes

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