Hydrochloric Acid → HCID 15713260, compound

HRID 1090168Notes

Reaction equation

HRID 1090168 reaction equation
[OH-].[Na+].[F:3][CH:4]([F:20])[C:5]1([C:15]([O:17]CC)=[O:16])[CH2:10][C:9](=[CH2:11])[CH2:8][CH:7]([C:12]([O-:14])=[O:13])[NH:6]1.Cl>C(O)C>[F:20][CH:4]([F:3])[C:5]1([C:15]([OH:17])=[O:16])[CH2:10][C:9](=[CH2:11])[CH2:8][CH:7]([C:12]([OH:14])=[O:13])[NH:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86745384HCID 86745384, compound

Product 1

HCID 15713260HCID 15713260, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.3 ml of 2N sodium hydroxide were added to a solution of 190 mg of the product of Example 13 (Isomer B) in 7 ml of ethanol and the mixture was stirred at ambient temperature for 30 hours and then neutralized to about pH 5 with 2N hydrochloric acid. After evaporating to dryness, the residue was taken up in 5 ml of water, then chromatographed on Dowex resin followed by elution with water. After evaporation to dryness, 140 mg of the product were taken up in 200 ml of water, filtered and lyophilized to obtain 130 mg of the desired product with a Rf=0.4 Butanol-acetic acid-water (4-2-2).

Workup

  1. customAfter evaporating to dryness
  2. customchromatographed on Dowex resin
  3. washfollowed by elution with water
  4. customAfter evaporation to dryness, 140 mg of the product
  5. filtrationfiltered

Sources & evidence

ORD record
ord-e432867bde074ba2b87520767601fe90
Source dataset
uspto-grants-1992_01
Patent number
US05081135

Reaction notes

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