Trifluoroacetic acid → HCID 12018741, compound

HRID 1860671Notes

Reaction equation

HRID 1860671 reaction equation
[CH3:1][C:2]([C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)=[CH:12][CH:11]=1)[CH2:3][C:4]([O:6]CC)=[O:5].FC(F)(F)C(O)=O>CO.[OH-].[Na+]>[CH3:1][C:2]([C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)([CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)=[CH:14][CH:15]=1)[CH2:3][C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 12018740HCID 12018740, compound

Product 1

HCID 12018741HCID 12018741, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

The product of STEP 9 (148 mg, 0.35 mmol) was dissolved in 5 ml methanol and 5 ml 1N sodium hydroxide solution. The reaction was stirred at room temperature for 18 h, acidified with 2 ml trifluoroacetic acid, and concentrated. The residue was purified on HPLC using acetonitrile gradient 10-50% in 30 min to yield 90.6 mg. FAB-MS:(MH+)=406.5. H NMR (DMSO-d6) δ1.43 (s, 3H), 2.03 (p, 2H), 2.61 (d, 1H), 2.92 (d,1IH), 2.96 (d, 1H), 3.07 (d, 1H), 3.48 (t, 2H), 4.01 (t, 2H), 6.76 (s, 4H), 6.85 (t,1H), 7.06 (d, 1H), 7.88 (m, 2H), 7.93 (d, 1H), 8.40 (d, 1H), 8.72 (d,1H), 8.76 (s, 1H), 8.90 (br, 1H); Anal Calcd. for C24H27N3O3 plus 2.75 CF3COOH: C, 48.67; H, 4.26; N, 5.77. Found: 48.56; H, 4.29; N, 6.05.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified on HPLC
  3. customin 30 min
  4. customto yield 90.6 mg

Sources & evidence

ORD record
ord-5db6b5743b824fa88c8f5fa9216430f1
Source dataset
uspto-grants-2003_03
Patent number
US06531494B1

Reaction notes

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