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

HRID 49401

Reaction equation

HRID 49401 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-65563c80684040c5aa909fa93bd0af8f
Source dataset
uspto-grants-2004_03
Patent number
US06706743B2

Linked notes

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