Trifluoroacetic acid → HCID 22319473, compound

HRID 897138Notes

Reaction equation

HRID 897138 reaction equation
[O:1]1[CH2:6][CH2:5][NH:4][C:3]2[N:7]=[C:8]([CH2:11][CH2:12][O:13][C:14]3[CH:19]=[CH:18][C:17]([CH:20]4[CH2:22][CH:21]4[CH2:23][C:24]([O:26]CC)=[O:25])=[CH:16][CH:15]=3)[CH:9]=[CH:10][C:2]1=2.FC(F)(F)C(O)=O>CO.[OH-].[Na+]>[O:1]1[CH2:6][CH2:5][NH:4][C:3]2[N:7]=[C:8]([CH2:11][CH2:12][O:13][C:14]3[CH:19]=[CH:18][C:17]([CH:20]4[CH2:22][CH:21]4[CH2:23][C:24]([OH:26])=[O:25])=[CH:16][CH:15]=3)[CH:9]=[CH:10][C:2]1=2

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 20792277HCID 20792277, compound

Product 1

HCID 22319473HCID 22319473, compoundYield 59.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

The product of step 7 (380 mg, 1 mmol) was dissolved in 5 ml methanol and 2.5 ml 1 N sodium hydroxide solution. The reaction was stirred at room temperature for 18 h, acidified with 1 ml trifluoroacetic acid, and concentrated. The residue was purified on HPLC using acetonitrile gradient 15-50% in 30 min to yield 210 mg desired product as an yellow oil. FAB-MS:(MH+)=355. H MNR(CDCl3) δ 0.78 (m, 1H), 0.86 (m, 1H), 1.21 (m, 1H), 1.70 (m, 1H), 2.35 (m, 2H), 3.12 (t, 2H), 3.63 (t, 2H), 4.22 (t, 2H), 4.26 (t, 2H), 6.65 (d, 1H), 6.79 (d, 2H), 7.0 (d, 2H), 7.6 (d, 1H). Anal Calcd. for C20H22N2O4 plus 1 CF3COOH and 0.2 H2O: C, 55.98; H, 5.00; N, 5.93. Found: 55.90; H, 5.28; N, 5.24.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified on HPLC
  3. customin 30 min

Sources & evidence

ORD record
ord-12f41148cfd743a38c62823a835cbea2
Source dataset
uspto-grants-2005_07
Patent number
US06921767B2

Reaction notes

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