Hydrochloric Acid → HCID 76578007, compound

HRID 910414Notes

Reaction equation

HRID 910414 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-60bccd2e41544944af287945ad9d37e5
Source dataset
uspto-grants-2011_09
Patent number
US08022092B2

Reaction notes

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