Chloride → HCID 22742102, compound

HRID 48171Notes

Reaction equation

HRID 48171 reaction equation
[Cl-].[NH2:2][C:3]1[CH:4]=[C:5]([CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:6]=[CH:7][C:8]=1[F:9]>N1C=CC=CC=1>[F:9][C:8]1[CH:7]=[CH:6][C:5]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:4][C:3]=1[NH:2][C:11](=[O:12])[CH2:10][CH:5]([CH3:6])[CH3:4]

Participants

4

Reactant 2

HCID 312ChlorideHCID 22742091HCID 22742091, compound

Product 1

HCID 22742102HCID 22742102, compoundYield 166%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Isovaleryll chloride (2.93 ml, 2.90 g, 0.024 mol) was added, dropwise, to a chilled (ice-bath) solution of methyl 3-amino-4-fluorophenylacetate (4.00 g, 0.022 mol) in pyridine (16 ml) and, once the addition was complete, the cooling bath was removed and the reaction mixture was stirred at room temperature for 30 minutes. The mixture was diluted with water and extracted with ethyl acetate. The organic extract was washed with water, dried over anhydrous magnesium sulfate, filtered and the filtrate was evaporated in vacuo. Trituration with dichloromethane/hexane gave methyl 4-fluoro-3-(3-methylbutyramido)phenylacetate (4.88 g) as a pale brown solid.

Workup

  1. additiononce the addition
  2. customthe cooling bath was removed
  3. additionThe mixture was diluted with water
  4. extractionextracted with ethyl acetate
  5. extractionThe organic extract
  6. washwas washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-e96a98a21ff145c187ae402f693a97ff
Source dataset
uspto-grants-2004_03
Patent number
US06703347B2

Reaction notes

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