Hydrochloric Acid → HCID 59389320, compound

HRID 2357949Notes

Reaction equation

HRID 2357949 reaction equation
[OH-:1].[Na+].[CH:3]([C:5]1[CH:23]=[C:8]2[C:9]([C:15]3[CH:16]([CH3:22])[CH2:17][C:18](=[O:21])[NH:19][N:20]=3)=[CH:10][CH:11]=[C:12]([O:13][CH3:14])[N:7]2[N:6]=1)=[O:4].Cl>[N+]([O-])([O-])=O.[Ag+]>[CH3:14][O:13][C:12]1[N:7]2[N:6]=[C:5]([C:3]([OH:1])=[O:4])[CH:23]=[C:8]2[C:9]([C:15]2[CH:16]([CH3:22])[CH2:17][C:18](=[O:21])[NH:19][N:20]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59389278HCID 59389278, compound

Product 1

HCID 59389320HCID 59389320, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 24470Silver NitrateCatalyst

Procedure

An aqueous solution (1 mL) of sodium hydroxide (41.9 mg) was added to an aqueous solution (3 mL) of silver nitrate (89.0 mg). To this mixture, the compound of Example 237 (60.0 mg) was added and the resulting mixture was stirred at room temperature for 1 hour. Subsequently, 5% hydrochloric acid was added to adjust the pH to 3. The insoluble material was separated by filtration and washed with a 7:1 mixture of chloroform and methanol. The filtrate and wash were combined. Sodium chloride was then added and the mixture was extracted with a 7:1 mixture of chloroform and methanol. The extract was dried over an hydrous magnesium sulfate and the solvent was evaporated. Methanol was added to the residue and the insoluble material was removed by filtration. The solvent of the filtrate was evaporated to afford the title compound as a pale yellow powder (46.3 mg).

Workup

  1. customThe insoluble material was separated by filtration
  2. washwashed with a 7:1 mixture of chloroform and methanol
  3. washThe filtrate and wash
  4. additionSodium chloride was then added
  5. extractionthe mixture was extracted with a 7:1 mixture of chloroform and methanol
  6. dry with materialThe extract was dried over an hydrous magnesium sulfate
  7. customthe solvent was evaporated
  8. additionMethanol was added to the residue
  9. customthe insoluble material was removed by filtration
  10. customThe solvent of the filtrate was evaporated

Sources & evidence

ORD record
ord-fd6e1f00250648ecad90de18a7d3b376
Source dataset
uspto-grants-2010_07
Patent number
US07763617B2

Reaction notes

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