Hydrochloric Acid → HCID 68862487, compound

HRID 1725915Notes

Reaction equation

HRID 1725915 reaction equation
[Cl:1][C:2]1[C:3]([NH:16][S:17]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)(=[O:19])=[O:18])=[C:4]([C:12]([O:14]C)=[O:13])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[Li+].[OH-].Cl.C(OCC)(=O)C>O1CCOCC1.O>[Cl:1][C:2]1[C:3]([NH:16][S:17]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)(=[O:19])=[O:18])=[C:4]([C:12]([OH:14])=[O:13])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 68863189HCID 68863189, compound

Product 1

HCID 68862487HCID 68862487, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of Example 146B in dioxane (3 mL) and water (0.3 mL) was treated with 3N LiOH (0.6 mL); stirred at 50° C. for 4 days, acidified with 1N HCl, treated with ethyl acetate, washed with brine (3×), dried (MgSO4), filtered, and concentrated and ethyl acetate was added. The ethyl acetate layer was washed with brine (3×), dried over magnesium sulfate anhydrous. The concentrate was purified by reverse phase chromatography to provide 1.5 mg of the desired product. MS (ESI(−)) m/e 346 (M−H)−.

Workup

  1. washwashed with brine (3×)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. additionethyl acetate was added
  6. washThe ethyl acetate layer was washed with brine (3×)
  7. dry with materialdried over magnesium sulfate anhydrous
  8. customThe concentrate was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-f707847b28ff4acea48c4b82c4a0af2e
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

Loading…