(+-)-Methionine → 4-(1,2-Oxazol-4-yl)phenol

HRID 413310Notes

Reaction equation

HRID 413310 reaction equation
NC(C(O)=O)CCSC.C[O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]=[N:20][O:21][CH:22]=2)=[CH:14][CH:13]=1.CS(O)(=O)=O>>[O:21]1[CH:22]=[C:18]([C:15]2[CH:14]=[CH:13][C:12]([OH:11])=[CH:17][CH:16]=2)[CH:19]=[N:20]1

Participants

4

Reactant 3

HCID 876(+-)-MethionineHCID 6395Methanesulfonic AcidHCID 185236724-(4-Methoxyphenyl)-1,2-oxazole

Product 1

HCID 185236244-(1,2-Oxazol-4-yl)phenolYield 68.2%

Conditions

Temperature
70 °C

Procedure

To a round-bottomed flask was added D,L-methionine (1.30 g, 8.73 mmol), 4-(4-methoxy-phenyl)-isoxazole (1.02 g, 5.82 mmol), and methanesulfonic acid (24 ml). The resulting solution was heated to about 70° C. for about eighteen hours, and was then allowed to cool to room temperature and poured onto ice water. The mixture was adjusted to about pH 4, and the heterogenous mixture was filtered. The solid was washed with water and then dried to yield the title compound as an off-white solid (640 mg, 68% yield). LRMS ([M−H]−)=160.0.

Workup

  1. temperatureto cool to room temperature
  2. additionpoured onto ice water
  3. filtrationthe heterogenous mixture was filtered
  4. washThe solid was washed with water
  5. customdried

Sources & evidence

ORD record
ord-5a9da30399f1484a9dbe3dbf570ff30f
Source dataset
uspto-grants-2003_05
Patent number
US06566377B2

Reaction notes

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