Hydrochloric Acid → HCID 58760759, compound

HRID 857399Notes

Reaction equation

HRID 857399 reaction equation
C([CH:3]([CH:7]1[C:11]2=[C:12]([S:24][C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)[C:13]3[C:14]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:15][C:16]([F:19])=[CH:17][C:18]=3[N:10]2[C:9](=[O:32])[CH2:8]1)[C:4]([O-:6])=[O:5])C.Cl>CC(=O)CC.O>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([S:24][C:12]2[C:13]3[C:14]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:15][C:16]([F:19])=[CH:17][C:18]=3[N:10]3[C:9](=[O:32])[CH2:8][CH:7]([CH2:3][C:4]([OH:6])=[O:5])[C:11]=23)=[CH:26][CH:27]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131726150HCID 131726150, compound

Product 1

HCID 58760759HCID 58760759, compoundYield 60.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
80 °C

Procedure

To the compound of Step 7 (40 mg) in 2-butanone (4 mL) was added 6N HCl (0.5 mL). The mixture was stirred at 80° C. for 3 hours, cooled to r.t., diluted with H2O and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography eluted with 40% EtOAc/hexane containing 1% AcOH to give 23 mg of the title compound as a white solid.

Workup

  1. temperaturecooled to r.t.
  2. extractionthe aqueous layer was extracted with EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography
  6. washeluted with 40% EtOAc/hexane containing 1% AcOH

Sources & evidence

ORD record
ord-c87d778053e64f62abd67e4ea4f1ee10
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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