Sodium Hydroxide → HCID 21310880, compound

HRID 583382Notes

Reaction equation

HRID 583382 reaction equation
C[O:2][C:3](=[O:35])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[C:5]=1[N:16]([S:24]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)(=[O:26])=[O:25])[CH2:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1.[OH-].[Na+]>C1COCC1.CO>[CH3:34][O:33][C:30]1[CH:31]=[CH:32][C:27]([S:24]([N:16]([CH2:17][C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[C:5]2[C:6]([CH2:10][N:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([OH:35])=[O:2])(=[O:26])=[O:25])=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70052803HCID 70052803, compound

Product 1

HCID 21310880HCID 21310880, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 0.754 g (1.523 mmol) of the product of Example 318 in 15 mL of THF/Methanol (1:1) was added 7.6 mL of 1.0N sodium hydroxide solution. The resulting mixture was heated to reflux for 15 h and then concentrated in vacuo. The residue was diluted with water, neutralized with 5% HCl solution and exited with dichloromethane. The organics were dried over Na2SO4, filtered and concentrated in vacuo to provide 0.496 g (67%) of the product as a tan solid. Electrospray Mass Spec: 482.5 (M+H)+.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 15 h
  3. concentrationconcentrated in vacuo
  4. additionThe residue was diluted with water
  5. dry with materialThe organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fac929c5b71749debe006559a77f93c1
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

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