Trifluoroacetic acid → HCID 19354624, compound

HRID 377575Notes

Reaction equation

HRID 377575 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[O:9][CH2:8][N:7]([C:10]([CH3:19])([CH3:18])[C:11]([O:13]C(C)(C)C)=[O:12])[C:6](=[O:20])[C:5]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][CH2:3][C:4]1[O:9][CH2:8][N:7]([C:10]([CH3:19])([CH3:18])[C:11]([OH:13])=[O:12])[C:6](=[O:20])[C:5]=1[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 54244127HCID 54244127, compound

Product 1

HCID 19354624HCID 19354624, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of tert butyl 2-(2,3-dihydro-6-methoxymethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoate (2.6 g) and trifluoroacetic acid (2.05 g) was stirred in dichloromethane for 20 hours at 35° C. A further addition of trifluoroacetic acid (0.82 g) was made and the solution heated under reflux for 24 hours. The cooled mixture was diluted (dichloromethane) and extracted (sodium carbonate solution). The aqueous extract was acidified (2 M hydrochloric acid solution), extracted (ethyl acetate), dried (magnesium sulphate) and evaporated. The residue was dissolved in ethyl acetate and evaporated (three times) redissolved in hexane and evaporated to give 2-(2,3-dihydro-6-methoxymethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoic acid (1.74 g) as a white solid, m.p. 135-138° C.

Workup

  1. temperaturethe solution heated
  2. temperatureunder reflux for 24 hours
  3. extractionextracted (sodium carbonate solution)
  4. extractionThe aqueous extract
  5. extractionextracted (ethyl acetate)
  6. dry with materialdried (magnesium sulphate)
  7. customevaporated
  8. dissolutionThe residue was dissolved in ethyl acetate
  9. customevaporated (three times)
  10. dissolutionredissolved in hexane
  11. customevaporated

Sources & evidence

ORD record
ord-bd90bfd444764749b007da3f1f08a0ec
Source dataset
uspto-grants-2000_02
Patent number
US06028032

Reaction notes

Loading…