Methanol → HCID 9997733, compound

HRID 5035Notes

Reaction equation

HRID 5035 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 10N sodium hydroxide aqueous solution. The solvent was distilled off under reduced pressure and 4N 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 4N 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-af4c10d538844fb08c46cdd882fe2355
Source dataset
uspto-grants-1993_09
Patent number
US05242931

Reaction notes

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