Trifluoroacetic acid → HCID 10225183, compound

HRID 1860658Notes

Reaction equation

HRID 1860658 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:20][C:21]([CH3:29])([CH3:28])[CH2:22][C:23]([O:25]CC)=[O:24])[CH:5]=[C:6]([F:19])[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+]>[Br:1][C:2]1[CH:3]=[C:4]([CH2:20][C:21]([CH3:29])([CH3:28])[CH2:22][C:23]([OH:25])=[O:24])[CH:5]=[C:6]([F:19])[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 12018738HCID 12018738, compound

Product 1

HCID 10225183HCID 10225183, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

The product of STEP 9 (0.254 g, 0.54 mmol) was dissolved in 10 ml methanol and 10 ml 1 N sodium hydroxide solution. The reaction was stirred at room temperature for 18 h, and acidified with trifluoroacetic acid (5 ml). Solvents were evaporated and residue was purified on HPLC using acetonitrile gradient 10-50% in 30 min to yield 0.213 g. NMR spectra of the product were consistent for the proposed structure. FAB-MS:(M+2)=441.3. H MNR (CDCl3) δ1.05 (s, 6H), 2.20 (p, 2H), 2.22 (s, 2H), 2.63 (s, 2H), 2.68 (q, 2H), 4.20 (t, 2H), 6.74 (t, 1H), 6.93 (dd, 1H), 6.97 (s, 1H), 7.15 (s, 1H), 7.83 (m, 2H), 9.66 (br, 1H); Anal Calcd. for C20H24N2O3FBr plus 1.75 CF3COOH: C, 44.18; H, 4.06; N, 4.38. Found: 44.05; H, 4.16; N, 4.25.

Workup

  1. customSolvents were evaporated
  2. customresidue was purified on HPLC
  3. customin 30 min
  4. customto yield 0.213 g

Sources & evidence

ORD record
ord-3cd8a11a4ea24cd9ba0985e7b40242a8
Source dataset
uspto-grants-2003_03
Patent number
US06531494B1

Reaction notes

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