Methane → HCID 21480145, compound

HRID 2259672Notes

Reaction equation

HRID 2259672 reaction equation
[OH:1][C:2]([CH2:7][F:8])([CH3:6])[C:3](O)=[O:4].S(Cl)(Cl)=O.C1(S([C:22]2[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=2)(=O)=O)C=CC=CC=1.[CH4:29].[CH3:30][C:31](N(C)C)=[O:32]>>[C:30]1([C:31]([C:22]2[CH:23]=[CH:24][C:25]([NH:26][C:3](=[O:4])[C:2]([OH:1])([CH3:6])[CH2:7][F:8])=[CH:27][CH:28]=2)=[O:32])[CH:24]=[CH:23][CH:22]=[CH:28][CH:29]=1

Participants

6

Reactant 5

HCID 297MethaneHCID 24386Thionyl ChlorideHCID 31374DimethylacetamideHCID 5166664-(Phenylsulfonyl)anilineHCID 14786033Propanoic acid, 3-fluoro-2-hydroxy-2-methyl-

Product 1

HCID 21480145HCID 21480145, compound

Conditions

Temperature
-10 °C

Procedure

A solution of 2-hydroxy-2-fluoromethylpropionic acid (0.93 g, 7.65 mmol) in dry dimethylacetamide (20 ml) was stirred under a nitrogen atmosphere at -10° C. Thionyl chloride (0.91 g, 7.65 mmol) was added and the resulting mixture was allowed to stir at -10° C. for 1 hour. 4-Phenylsulfonylaniline (1.0 g, 4.29 mmol) was then added and the reaction mixture was stirred at -10° C. for a further 15 mins. The solution was then allowed to warm to room temperature where it was stirred overnight. The reaction mixture was poured onto water, extracted with ethyl acetate, and the combined ethyl acetate portions were washed with water, and brine. After drying (Na2SO4) the ethyl acetate was removed by evaporation to give an stray-colored foam. Chromatography on silica gel, eluting with ethyl acetate/hexane (1:1) gave the tertiary carbinol (0.75 g, 48%) as a white powder; mp=146°-148° C. 1H-NMR (300 MHz, d6 -DMSO): 1.36 (s, 3H, CH3), 4.38 (dd, J=72 and 9.4 Hz, 1H, CH2F), 4.58 (dd, J=72 and 9.3 Hz, 1H, CH2F), 6.32 (s, 1H, OH), 7.56 (t, J=7.7 Hz, 2H, ArH), 7.65-7.76 (m, 5H, ArH), 7.97 (d, J=8.7 Hz, 2H, ArH), 10.08 (s, 1H, NH). MS (CI, CH4): 302(M+1, 100). Analysis for C17H16FNO3 : Calculated: C, 67.76; H, 5.35; N, 4.65 Found: C, 67.45; H, 5.41; N, 4.58

Workup

  1. stirringthe reaction mixture was stirred at -10° C. for a further 15 mins
  2. temperatureto warm to room temperature where it
  3. stirringwas stirred overnight
  4. additionThe reaction mixture was poured onto water
  5. extractionextracted with ethyl acetate
  6. washthe combined ethyl acetate portions were washed with water, and brine
  7. dry with materialAfter drying (Na2SO4) the ethyl acetate
  8. customwas removed by evaporation
  9. customto give an stray-colored foam
  10. washChromatography on silica gel, eluting with ethyl acetate/hexane (1:1)
  11. customgave the tertiary carbinol (0.75 g, 48%) as a white powder

Sources & evidence

ORD record
ord-21bee70816d04188932beadbbe70e0c7
Source dataset
uspto-grants-1995_12
Patent number
US05474999

Reaction notes

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