Hydrochloric Acid → HCID 10735574, compound

HRID 1736184Notes

Reaction equation

HRID 1736184 reaction equation
Cl.[F:2][C:3]1[C:4]([CH2:36][OH:37])=[C:5]([F:35])[C:6]2[O:11][C:10]([C:12]3[CH:17]=[CH:16][C:15]([NH:18]C(=O)C(C)(C)C)=[C:14]([F:25])[CH:13]=3)=[CH:9][C:8](=[O:26])[C:7]=2[C:27]=1[NH:28]C(=O)C(C)(C)C.[OH-].[Na+]>C(O)C>[NH2:28][C:27]1[C:7]2[C:8](=[O:26])[CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([F:25])[CH:13]=3)[O:11][C:6]=2[C:5]([F:35])=[C:4]([CH2:36][OH:37])[C:3]=1[F:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10673123HCID 10673123, compound

Product 1

HCID 10735574HCID 10735574, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

40 mL of ethanol and 20 mL of concentrated hydrochloric acid were added to 903 mg (1.79 mmol) of the above 6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-7-hydroxymethyl-5-pivaloylamino-4H-1-benzopyran-4-one and the mixture was heated at reflux for 6.5 hours. The reaction solution was cooled on ice and adjusted to pH 7 to 8 by addition of a 10N aqueous solution of sodium hydroxide thereto, and the precipitated crystals were collected by filtration. The crystals were purified by silica gel column chromatography (chloroform:methanol=40:1-9:1) and triturated with ethyl acetate to give 364 mg of Compound 118 (yield: 60%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 6.5 hours
  3. temperatureThe reaction solution was cooled on ice
  4. filtrationthe precipitated crystals were collected by filtration
  5. customThe crystals were purified by silica gel column chromatography (chloroform:methanol=40:1-9:1)
  6. customtriturated with ethyl acetate

Sources & evidence

ORD record
ord-53000b33c4cd4b17a0854bd99eb9b32a
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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