3-Bromo-1,1,1-trifluoro-2-propanone → HCID 66636924, compound

HRID 1094319Notes

Reaction equation

HRID 1094319 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]([CH3:16])[C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=1)(=[O:3])[NH2:2].Br[CH2:18][C:19](=O)[C:20]([F:23])([F:22])[F:21]>O1CCOCC1>[F:21][C:20]([F:23])([F:22])[C:19]1[N:2]=[C:1]([NH:4][C:5]2[CH:6]=[CH:7][C:8]([C@@H:11]([CH3:16])[C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[O:3][CH:18]=1

Participants

4

Reactant 2

HCID 790083-Bromo-1,1,1-trifluoro-2-propanoneHCID 66636739HCID 66636739, compound

Product 1

HCID 66636924HCID 66636924, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of methyl (2R)-2-[4-(carbamoylamino)phenyl]propanoate (2.7 g, 9.95 mmol) in dioxane (50 ml) was treated at room temperature with 3-bromo-1,1,1-trifluoro-propan-2-one (1.03 ml, 10 mmol) and the resulting mixture was refluxed for 2 h. After cooling at room temperature, the solvent was evaporated under vacuum, the crude diluted with CH2Cl2 (50 ml) and washed with a saturated NaHCO3 aqueous solution (3×30 ml), dried over anhydrous Na2SO4 and evaporated to give pure methyl (2R)-2-(4-{[4-(trifluoromethyl)-1,3-oxazol-2-yl]amino}phenyl)propanoate (2.5 g, 7.96 mmol) as yellow oil (80%). 1H-NMR (CDCl3): δ 10.05 (bs, 1H, NH), 8.30 (s, 1H), 7.45 (d, 2H, J=7 Hz), 7.25 (d, 2H, J=7 Hz), 3.75 (q, 1H, J=7 Hz), 3.65 (s, 3H), 1.50 (d, 3H, J=7 Hz).

Workup

  1. temperaturethe resulting mixture was refluxed for 2 h
  2. customthe solvent was evaporated under vacuum
  3. additionthe crude diluted with CH2Cl2 (50 ml)
  4. washwashed with a saturated NaHCO3 aqueous solution (3×30 ml)
  5. dry with materialdried over anhydrous Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-b13bda5c4fe44cf2a2653b227c7d3f74
Source dataset
uspto-grants-2012_03
Patent number
US08133911B2

Reaction notes

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