Ethanol → HCID 21084005, compound

HRID 347923Notes

Reaction equation

HRID 347923 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[C:21](=[O:22])[CH:20]=[CH:19][C:18]4[C:23]([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)=[C:24]([C:26]([O:28]CC)=[O:27])[S:25][C:17]3=4)=[CH:12][CH:11]=2)[CH2:3][CH2:2]1.[OH-].[Na+].CCO>O>[O:1]1[CH2:2][CH2:3][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]([N:16]3[C:21](=[O:22])[CH:20]=[CH:19][C:18]4[C:23]([C:31]5[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=5)=[C:24]([C:26]([OH:28])=[O:27])[S:25][C:17]3=4)=[CH:14][CH:15]=2)[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 21084060HCID 21084060, compound

Product 1

HCID 21084005HCID 21084005, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the compound of Example 92 (230 mg, 0.46 mmol), sodium hydroxide (91 mg, 2.28 mmol) and EtOH (5 mL) was heated at reflux for 18 h. EtOH was removed in vacuo and the residue treated with 2M HCl(aq) (2 mL) to give a white solid. The reaction was diluted with water and then freeze dried. The resultant solid was extracted with isopropanol and the extracts concentrated in vacuo to give the title compound as a white solid (97 mg). δH (DMSO-d6) 7.62–7.37 (8H, m), 7.21–7.16 (2H, m), 6.50 (1H, J 9.6 Hz), 4.20 (2H, t, J 5.7 Hz), 3.62–3.59 (4H, m), 2.76 (2H, t, J 5.7 Hz), 2.54–2.51 (4H, m). LCMS (ES+) RT 2.35 minutes, 477 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. customEtOH was removed in vacuo
  4. additionthe residue treated with 2M HCl(aq) (2 mL)
  5. customto give a white solid
  6. customfreeze dried
  7. extractionThe resultant solid was extracted with isopropanol
  8. concentrationthe extracts concentrated in vacuo

Sources & evidence

ORD record
ord-f1f3f7634593436a8a8353bbf4db5b6b
Source dataset
uspto-grants-2007_02
Patent number
US07176215B2

Reaction notes

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