Water → HCID 19958021, compound

HRID 1769311Notes

Reaction equation

HRID 1769311 reaction equation
[C:1]1([CH:7]([C:15]([OH:17])=[O:16])[NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[CH3:19].[H-].[Na+].O>O1CCCC1.C(OCC)(=O)C>[C:1]1([CH:7]([C:15]([OH:17])=[O:16])[N:8]([C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])[CH3:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydride2×HCID 3509812HCID 3509812, compound

Product 1

HCID 19958021HCID 19958021, compoundYield 19.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-phenyl-N-(trifluoroacetyl)-glycine (2.5 g, 0.01 mol) and iodomethane (11.35 g, 0.08 mol) in tetrahydrofuran is treated portionwise with a 60% dispersion of sodium hydride in mineral oil (1.2 g, 0.03 mol NaH), stirred at ambient temperatures for 1 hour, heated at reflux temperature for 17 hours, cooled to room temperature, diluted with ethyl acetate followed by 1 mL of water and concentrated in vacuo to a wet yellow solid residue. The residue is dispersed in a mixture of ether and water. The ether layer is washed with a sodium bicarbonate solution. The aqueous phases are combined, acidified with 10% HCl and extracted with ethyl acetate. The ethyl acetate extract is washed sequentially with water, sodium thiosulfate and saturated sodium chloride solution, dried over MgSO4 and concentrated in vacuo to give a pale yellow solid which is recrystallized for methylcyclohexane to give the title compound as white crystals, 0.5 g, (19.1% yield), mp 124°-126° C.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 17 hours
  3. concentrationconcentrated in vacuo to a wet yellow solid residue
  4. additionThe residue is dispersed in a mixture of ether and water
  5. washThe ether layer is washed with a sodium bicarbonate solution
  6. extractionextracted with ethyl acetate
  7. extractionThe ethyl acetate extract
  8. washis washed sequentially with water, sodium thiosulfate and saturated sodium chloride solution
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated in vacuo
  11. customto give a pale yellow solid which
  12. customis recrystallized for methylcyclohexane

Sources & evidence

ORD record
ord-0ec7d23de691459d8660de921be1e302
Source dataset
uspto-grants-1995_01
Patent number
US05380876

Reaction notes

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