Methane → HCID 21480109, compound

HRID 865742Notes

Reaction equation

HRID 865742 reaction equation
[OH:1][C:2]([CH2:7][F:8])([CH3:6])[C:3](O)=[O:4].S(Cl)(Cl)=O.[C:13]1([S:19]([C:22]2[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH:18]=[CH:17]C=[CH:15][CH:14]=1.C(=O)(O)[O-].[Na+].C.CC([N:38](C)C)=O>>[N:38]1[CH:17]=[CH:18][C:13]([S:19]([C:22]2[CH:28]=[CH:27][C:25]([NH:26][C:3](=[O:4])[C:2]([OH:1])([CH3:6])[CH2:7][F:8])=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[CH:14][CH:15]=1

Participants

7

Reactant 6

HCID 297MethaneHCID 24386Thionyl ChlorideHCID 31374DimethylacetamideHCID 5166664-(Phenylsulfonyl)anilineHCID 516892Sodium BicarbonateHCID 14786033Propanoic acid, 3-fluoro-2-hydroxy-2-methyl-

Product 1

HCID 21480109HCID 21480109, compound

Conditions

Temperature
-10 °C

Procedure

A solution of 2-hydroxy-2-fluoromethylpropionic acid (0.53 g, 4.33 mmol) in dry dimethylacetamide (12 ml) was stirred under a nitrogen atmosphere at -10° C. Thionyl chloride (0.52 g, 4.33 mmol) was added and the resulting mixture was allowed to stir at -10° C. for 1 hour. 4-Phenylsulfonylaniline (0.68 g, 2.89 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 and the pH adjusted to pH 8.0 with sodium bicarbonate solution. The aqueous solution was 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 a yellow-orange solid. The solid was washed with ether/methylene chloride to yield the title tertiary carbinol (0.32 g, 32%) as a pale yellow solid; mp=209°-211° C. 1H-NMR (300 MHz, d6 -DMSO): 1.31 (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), 6.31 (s, 1H, OH), 7.87 (d, J=6 Hz, 2H, PyH), 7.96 (d, J=8.9 Hz, 2H, PhH), 8.06 (d, J=8.9 Hz, 2H, PhH), 8.86 (d, J=6 Hz, 2H, PyH), 10.22 (s, 1H, NH). MS (CI, CH4): 339(M+1, 100).

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. extractionThe aqueous solution was extracted 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 a yellow-orange solid
  10. washThe solid was washed with ether/methylene chloride
  11. customto yield the title tertiary carbinol (0.32 g, 32%) as a pale yellow solid

Sources & evidence

ORD record
ord-927f3cbc5bf9469cafaf1d47aaf961b5
Source dataset
uspto-grants-1996_10
Patent number
US05567735

Reaction notes

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