Sodium Hydroxide → HCID 19434813, compound

HRID 1736221Notes

Reaction equation

HRID 1736221 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[C:18]([F:19])=[CH:17][C:16]([F:20])=[C:15]([NH:21][CH2:22][C:23]([O:25]CC)=[O:24])[C:11]=3[C:12](=[O:14])[CH:13]=2)=[CH:4][C:3]=1[F:28].[OH-].[Na+]>C(O)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[C:18]([F:19])=[CH:17][C:16]([F:20])=[C:15]([NH:21][CH2:22][C:23]([OH:25])=[O:24])[C:11]=3[C:12](=[O:14])[CH:13]=2)=[CH:4][C:3]=1[F:28]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19435007HCID 19435007, compound

Product 1

HCID 19434813HCID 19434813, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

305 mg (0.779 mmol) of the above 2-(4-amino-3-fluorophenyl)-5-ethoxycarbonylmethylamino-6,8-difluoro-4H-1-benzopyran-4-one was dissolved in 20 mL of ethanol, a 2N aqueous solution of sodium hydroxide was added and the mixture was stirred at 50° C. for 40 minutes. The reaction solution was cooled on ice and the crystals were collected by filtration. The crystals were suspended in water, the suspension was adjusted to pH 2 by addition of hydrochloric acid thereto, and the crystals were collected by filtration again and purified by silica gel column chromatography (chloroform:methanol:acetic acid=90:10:1) to give 148 mg of Compound 140 (yield: 52%).

Workup

  1. temperatureThe reaction solution was cooled on ice
  2. filtrationthe crystals were collected by filtration
  3. additionthe suspension was adjusted to pH 2 by addition of hydrochloric acid
  4. filtrationthe crystals were collected by filtration again
  5. custompurified by silica gel column chromatography (chloroform:methanol:acetic acid=90:10:1)

Sources & evidence

ORD record
ord-7b8da1bf32f3427095dabd1edbc797d7
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

Loading…