3-Fluorophenylacetic acid → HCID 70278077, compound

HRID 582490Notes

Reaction equation

HRID 582490 reaction equation
O[C:2]([CH3:14])([CH3:13])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11]C)=CC=1)=O.[F:15][C:16]1[CH:17]=[C:18]([CH2:22][C:23]([OH:25])=[O:24])[CH:19]=[CH:20][CH:21]=1.[CH2:26]1CCN2C(=NCCC2)CC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:14][C:2]1([CH3:13])[O:24][C:23](=[O:25])[C:22]([C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([F:15])[CH:17]=2)=[C:3]1[C:5]1[S:11][CH:8]=[C:9]([CH3:26])[CH:10]=1

Participants

6

Reactant 3

HCID 676173-Fluorophenylacetic acidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 114131682-Hydroxy-4'(methylthio)isobutyrophenone

Product 1

HCID 70278077HCID 70278077, compoundYield 173.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a room temperature solution of 2-hydroxy-2-methyl-1-(4-methylthiophenyl)-propan-1-one (WO 95/00501, 20.0 g, 95.1 mmol), 3-fluorophenylacetic acid (29.3 g, 190 mmol) and DMAP (1.16 g, 9.5 mmol) in 500 mL of CH2Cl2 was added CMC (80.5 g, 190.2 mmol). The resulting mixture was stirred for 16 h under nitrogen. DBU (46 mL, 301 mmol) was then added, and the mixture stirred for 1.5 h. The reaction was quenched with 1M HCl, and the organic phase was washed with saturated aqueous NaHCO3 and brine. The CH2Cl2 layer wa filtered through cotton and concentrated to give 50 g of the title compound, which was used in Step 2 without further purification.

Workup

  1. stirringthe mixture stirred for 1.5 h
  2. customThe reaction was quenched with 1M HCl
  3. washthe organic phase was washed with saturated aqueous NaHCO3 and brine
  4. filtrationThe CH2Cl2 layer wa filtered through cotton
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-956326b724b84608bfd07acbf20bba15
Source dataset
uspto-grants-1999_07
Patent number
US05925631

Reaction notes

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