Sodium Hydroxide → HCID 11845294, compound

HRID 1366890Notes

Reaction equation

HRID 1366890 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1[NH:8][CH:9]=[C:10]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]=1)=[O:6]>CO>[CH2:12]([C:10]1[CH:11]=[C:7]([C:5]([OH:6])=[O:4])[NH:8][CH:9]=1)[CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57435078HCID 57435078, compound

Product 1

HCID 11845294HCID 11845294, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Freshly prepared aq. NaOH (10 M in H2O, 1.65 mmol) was added to a stirring, room temperature solution of 27 (0.0755 g, 0.329 mmol) in MeOH (0.82 mL, 0.4 M) under N2. Another 0.7 mL of MeOH was added due to precipitation of the starting material, and the reaction was heated to reflux until the reaction was judged complete by HPLC (2 h): The reaction was concentrated and then dissolved in 0.55 mL H2O. 10% aq. HCl was added dropwise until the pH=2. The white solid that precipitated from the reaction was filtered off and washed with cold H2O. The solid was dried under vacuum overnight to obtain pure 28. 1H (CDCl3, 400 MHz): δ 10.87 (1H, broad s), 7.25-7.18 (2H, m), 7.17-7.69 (3H, m), 6.70 (1H, s), 6.67 (1H, s), 2.83 (2H, t, J=7.6 Hz), 2.74 (2H, t, J=7.6 Hz) ppm. 13C (CDCl3, 100 MHz): δ 164.53, 143.39, 129.50, 129.21, 126.76, 126.38, 123.49, 122.85, 116.48, 38.68, 29.94 ppm. DEPT (CDCl3, 100 MHz): CH2 carbons: 38.68, 29.94; CH carbons: 129.50, 129.21, 126.76, 122.85, 116.48 ppm. HPLC: 8.579 min.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux until the reaction
  3. customwas judged complete by HPLC (2 h)
  4. concentrationThe reaction was concentrated
  5. dissolutiondissolved in 0.55 mL H2O
  6. addition10% aq. HCl was added dropwise until the pH=2
  7. customThe white solid that precipitated from the reaction
  8. filtrationwas filtered off
  9. washwashed with cold H2O
  10. customThe solid was dried under vacuum overnight
  11. customto obtain pure 28
  12. custom8.579 min.

Sources & evidence

ORD record
ord-a933d0505a7c4037ae94a0663d3ebc6a
Source dataset
uspto-grants-2011_02
Patent number
US07893098B2

Reaction notes

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