Methane → HCID 21480142, compound

HRID 2259670Notes

Reaction equation

HRID 2259670 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][CH:16]=[CH:15][CH:14]=1.C>CC(N(C)C)=O.O.CO.CCOCC.C(Cl)Cl>[C:13]1([S:19]([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:20])=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

9

Reactant 4

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

Product 1

HCID 21480142HCID 21480142, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 31374DimethylacetamideSolventHCID 21881112Ethyl ether methylene chlorideSolvent

Conditions

Temperature
-10 °C

Procedure

A solution of 2-hydroxy-2-fluoromethylpropionic acid (0.78 g, 6.4 mmol) in dry dimethylacetamide (15 ml) was stirred under a nitrogen atmosphere at -10° C. Thionyl chloride (0.76 g, 6.4 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 amber foam. Trituration with ether/methylene chloride yielded the title tertiary carbinol (0.75 g, 52%) as a light tan solid; mp=189°-192° 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), 6.29 (s, 1H, OH), 7.58-7.68 (m, 4H, ArH, 7.89-8.02 (m, 5H, ArH), 10.16 (S, 1H, NH). MS (CI, CH4): 338(+1, 100). Analysis for C16H16FNO4S.0.1 H2O: Calculated: C, 56.66; H, 4.81 ; N, 4.13 Found: C, 56.40; H, 4.74; N, 4.02

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 amber foam

Sources & evidence

ORD record
ord-887228633d7a4f8686639013926ae703
Source dataset
uspto-grants-1995_12
Patent number
US05474999

Reaction notes

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