Sodium Hydroxide → HCID 16065088, compound

HRID 1991135Notes

Reaction equation

HRID 1991135 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([CH2:19][CH:20]([CH3:22])[CH3:21])[CH:18]=[C:13]3[C:12]([C:23]3[N:24]=[C:25]([CH:28]4[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]4)[S:26][CH:27]=3)=[CH:11]2)(=O)=O)C=CC=CC=1.[OH-].[Na+].C([O-])(O)=O.[Na+]>CCO>[CH2:19]([C:17]1[CH:18]=[C:13]2[C:12]([C:23]3[N:24]=[C:25]([CH:28]4[CH2:29][CH2:30][N:31]([CH3:34])[CH2:32][CH2:33]4)[S:26][CH:27]=3)=[CH:11][NH:10][C:14]2=[N:15][CH:16]=1)[CH:20]([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 59128662HCID 59128662, compound

Product 1

HCID 16065088HCID 16065088, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 76 (155 mg, 0.31 mmol) in EtOH (4 mL) was added 10% aqueous NaOH (2 mL) and the reaction was heated at reflux for 1.5 h. The mixture was then cooled. Saturated aqueous NaHCO3 (25 mL) was added, and the solution was extracted with AcOEt (2×40 mL) The combined organic extracts were dried (MgSO4) and concentrated to afford a brown solid, which was purified by preparative LCMS (column LUNA 10 μ C18(2) 00G-4253-V0 250×50 mm) using water—acetonitrile (0.1% AcOH) as eluent (in gradient; flow 80 mL/min) to afford 77 as a white solid (54 mg, 0.15 mmol, 49%). 1H NMR (400 MHz, CDCl3) δ 0.96 (d, J=6.6 Hz, 2H), 1.94 (nonet, J=6.7 Hz, 1H), 2.07-2.19 (m, 2H), 2.25-2.35 (m, 2H), 2.41-2.52 (m, 5H), 2.64 (d, J=7.1 Hz, 2H), 3.14-3.24 (m, 3H), 7.26 (s, 1H), 7.83 (s, 1H), 8.10 (d, J=1.9 Hz, 1H), 8.18 (d, J=1.9 Hz, 1H), 10.90 (br s, 1H). MS (CI) m/z 355 (MH+).

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 1.5 h
  3. temperatureThe mixture was then cooled
  4. extractionthe solution was extracted with AcOEt (2×40 mL) The combined organic extracts
  5. dry with materialwere dried (MgSO4)
  6. concentrationconcentrated
  7. customto afford a brown solid, which
  8. customwas purified by preparative LCMS (column LUNA 10 μ C18(2) 00G-4253-V0 250×50 mm)

Sources & evidence

ORD record
ord-3715dbcf709b48caaa0f3bb64a28fc67
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

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