Hydrochloric Acid → HCID 76578007, compound

HRID 2197265Notes

Reaction equation

HRID 2197265 reaction equation
C[O:2][C:3](=[O:31])[CH:4]([N:8]1[C:12](=[O:13])[CH:11]([CH2:14][O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=3)=[CH:19][CH:18]=2)[NH:10][C:9]1=[O:30])[CH:5]([CH3:7])[CH3:6].Cl>>[F:29][C:25]1[CH:24]=[C:23]([C:20]2[CH:19]=[CH:18][C:17]([CH2:16][O:15][CH2:14][CH:11]3[C:12](=[O:13])[N:8]([CH:4]([CH:5]([CH3:6])[CH3:7])[C:3]([OH:31])=[O:2])[C:9](=[O:30])[NH:10]3)=[CH:22][CH:21]=2)[CH:28]=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 76578052HCID 76578052, compound2×

Product 1

HCID 76578007HCID 76578007, compoundYield 46%

Procedure

A mixture of the compound obtained in step b above (20b) (374 mg, 0.874 mmol) and 2 N HCl (15 mL) was refluxed for 2 h. The reaction mixture was cooled down and then extracted with EtOAc. The combined organic layer was dried and concentrated; the crude product was purified by silica gel column chromatography to give the title compound as colorless oil (166 mg, 46%).

Workup

  1. temperaturewas refluxed for 2 h
  2. temperatureThe reaction mixture was cooled down
  3. extractionextracted with EtOAc
  4. customThe combined organic layer was dried
  5. concentrationconcentrated
  6. customthe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-fba574b42aa540d891761608237bb8be
Source dataset
uspto-grants-2012_12
Patent number
US08338471B2

Reaction notes

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