Methanol → HCID 15288037, compound

HRID 37716Notes

Reaction equation

HRID 37716 reaction equation
C([O:3][C:4](=[O:34])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH2:16][C:17]3[S:18][C:19]4[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=4[N:21]=3)[CH:13]=2)[N:8]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:7]=1[CH3:33])C.CO.[OH-].[Na+]>O1CCCC1>[S:18]1[C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=[C:17]1[CH2:16][O:15][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:7]([CH3:33])=[C:6]2[CH2:5][C:4]([OH:34])=[O:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 15288036HCID 15288036, compound

Product 1

HCID 15288037HCID 15288037, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution containing the compound of Example 50, (2.5 g, 5.31 mmol), methanol (200 mL), tetrahydrofuran (200 mL) and 1N sodium hydroxide (9.5 mL) is refluxed for 3 hours. Upon cooling, the mixture is concentrated under reduced pressure, diluted with water (200 mL) and acidified with 2 N HCl. After stirring for 30 minutes, the product is filtered and recrystallized from acetonitrile to give the title compound as a white solid in 85% yield, m.p. 186°-188° C.

Workup

  1. temperatureis refluxed for 3 hours
  2. temperatureUpon cooling
  3. concentrationthe mixture is concentrated under reduced pressure
  4. additiondiluted with water (200 mL)
  5. filtrationthe product is filtered
  6. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-3df581a963e84a7eb57529137691474b
Source dataset
uspto-grants-1995_05
Patent number
US05420289

Reaction notes

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