Acetic Acid → HCID 16064349, compound

HRID 1991120Notes

Reaction equation

HRID 1991120 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([NH:19][C:20]([C:22]4[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=4[C:24]([OH:26])=[O:25])=[O:21])[CH:18]=[C:13]3[C:12]([C:31]3[S:35][CH:34]=[N:33][CH:32]=3)=[CH:11]2)(=O)=O)C=CC=CC=1.[OH-].[Na+].C(O)(=O)C>CCO>[S:35]1[C:31]([C:12]2[C:13]3[C:14](=[N:15][CH:16]=[C:17]([NH:19][C:20]([C:22]4[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=4[C:24]([OH:26])=[O:25])=[O:21])[CH:18]=3)[NH:10][CH:11]=2)=[CH:32][N:33]=[CH:34]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 59128683HCID 59128683, compound

Product 1

HCID 16064349HCID 16064349, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sulfonamide 44 (20 mg, 40 μmol), 10% aqueous NaOH solution (0.36 mL, 0.9 mmol) in EtOH (1.0 mL) was refluxed for 30 min. The mixture was cooled, concentrated, treated with glacial acetic acid (0.72 mL, 12 mmol), and concentrated again. The residue was separated by LCMS (column LUNA 10 μ C18(2) 00G-4253-V0 250×50 mm) using water—MeCN (0.11% AcOH) as eluent (in gradient; flow 80 mL/min) to afford 45 (3.88 mg, 27%). 1H NMR (400 MHz; CDCl3+3 drops of CD3OD) δ 7.36 (dd, J=7.5, 2.5 Hz, 1H), 7.57 (s, 2H), 7.78 (s, 1H), 8.02 (d, J=2.0 Hz, 1H), 8.15 (d, J=1.8 Hz, 1H), 8.20 (d, J=1.9 Hz, 1H), 8.39 (d, J=2.1 Hz, 1H), 8.50 (s, 1H); MS (ES) m/z 406.3 (MH++MeCN).

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated
  3. concentrationconcentrated again
  4. customThe residue was separated by LCMS (column LUNA 10 μ C18(2) 00G-4253-V0 250×50 mm)

Sources & evidence

ORD record
ord-1ae6308b0e9148b293d616f991856205
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

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