Hydrochloric Acid → HCID 9816245, compound

HRID 1934349Notes

Reaction equation

HRID 1934349 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.CCCCCC.[OH:14][CH2:15][C:16]([NH:19][C:20](=[O:29])[C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=1[F:28])([CH3:18])[CH3:17].B(F)(F)F.CCOCC.Cl>C(Cl)Cl>[CH3:1][O:14][CH2:15][C:16]([NH:19][C:20](=[O:29])[C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=1[F:28])([CH3:18])[CH3:17]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8000Boron trifluoride etherateHCID 8058HexaneHCID 167693TrimethylsilyldiazomethaneHCID 98374972,4-Difluoro-N-(2-hydroxy-1,1-dimethylethyl)benzamide

Product 1

HCID 9816245HCID 9816245, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2M trimethylsilyldiazomethane in hexane (3.9 ml, 7.8 mmol) was added dropwise to a solution of N-(2-hydroxy-1,1-dimethylethyl)-2,4-difluorobenzamide obtained in Example 27 (0.59 g, 2.6 mmol) and boron trifluoride diethyl etherate (43 mg, 0.3 mmol) in methylene chloride (6 ml), and stirred at room temperature overnight. To the reaction mixture was added 1N hydrochloric acid (5 ml) dropwise, and the resulting mixture was concentrated and extracted with ethyl acetate. The extract was washed with brine, dried over MgSO4 and concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1) to give the title compound (0.38 g; 60%).

Workup

  1. concentrationthe resulting mixture was concentrated
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under a reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-de4fb4755d2242b8bc90c5ff82cf3f5f
Source dataset
uspto-grants-2002_05
Patent number
US06384033B1

Reaction notes

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