Methanol → HCID 9997733, compound

HRID 892486Notes

Reaction equation

HRID 892486 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][CH:9]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[CH2:13][O:12][C:11]3[CH:20]=[CH:21][C:22]([C:24]([O:26]CC)=[O:25])=[CH:23][C:10]2=3)[CH:2]=1.CO.[OH-].[Na+]>O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][CH:9]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[CH2:13][O:12][C:11]3[CH:20]=[CH:21][C:22]([C:24]([OH:26])=[O:25])=[CH:23][C:10]2=3)[CH:2]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 15704193HCID 15704193, compound

Product 1

HCID 9997733HCID 9997733, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Compound 9a, 3.9 g, obtained in Example 1 was heated to reflux for an hour in a solvent mixture of 200 ml of methanol, 50 ml of water and 10 ml of 10 N sodium hydroxide aqueous solution. The solvent was distilled off under reduced pressure and 4 N hydrochloric acid aqueous solution was added to the residue to adjust pH to 7. After concentrating under reduced pressure, the residue was subjected to high porous polymer (HP-10; manufactured by Mitsubishi Chemical Industry Co., Ltd.) column chromatography (eluting solvent; methanol) to give 2.5 g of the crude product. The crude product was recrystallized from water to give 2.0 g of the desired product.

Workup

  1. temperaturewas heated
  2. distillationThe solvent was distilled off under reduced pressure and 4 N hydrochloric acid aqueous solution
  3. additionwas added to the residue
  4. concentrationAfter concentrating under reduced pressure
  5. washthe residue was subjected to high porous polymer (HP-10; manufactured by Mitsubishi Chemical Industry Co., Ltd.) column chromatography (eluting solvent; methanol)
  6. customto give 2.5 g of the crude product
  7. customThe crude product was recrystallized from water

Sources & evidence

ORD record
ord-1ac83b2936564821bcfdef58d18f2628
Source dataset
uspto-grants-1992_06
Patent number
US05118701

Reaction notes

Loading…