Sodium Hydroxide → HCID 19034181, compound

HRID 265889Notes

Reaction equation

HRID 265889 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH2:15][CH2:16][O:17][C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24]C)=[O:23])=[CH:20][CH:19]=2)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH-].[Na+]>C(O)C>[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH2:15][CH2:16][O:17][C:18]2[CH:19]=[CH:20][C:21]([C:22]([OH:24])=[O:23])=[CH:26][CH:27]=2)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19034132HCID 19034132, compound

Product 1

HCID 19034181HCID 19034181, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 21-5 (1.6 g, 4.1 mmol), ethanol (41 mL), and 1N NaOH (21 mL) was stirred at ambient temperature for 20 hours. The reaction was then concentrated and the residue dissolved in H2O and then washed with ether. The aqueous phase was acidified with 5% KHSO4 and then extracted with EtOAc. The EtOAc portion was washed with 5% KHSO4 and brine, dried (MgSO4), and concentrated to furnish 21-6 as a white solid. TLC Rf =0.68 (silica, acetone);

Workup

  1. concentrationThe reaction was then concentrated
  2. dissolutionthe residue dissolved in H2O
  3. washwashed with ether
  4. extractionextracted with EtOAc
  5. washThe EtOAc portion was washed with 5% KHSO4 and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b562239eed164828a393884c357299ff
Source dataset
uspto-grants-1997_07
Patent number
US05648368

Reaction notes

Loading…