L-Methionine → 4-(4-[1,3,4]Oxadiazol-2-yl-phenoxy)-phenol

HRID 49147

Reaction equation

C[O:2][C:3]1[CH:20]=[CH:19][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[O:15][CH:16]=[N:17][N:18]=3)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.N[C@H](C(O)=O)CCSC.CS(O)(=O)=O>C(=O)(O)[O-].[Na+]>[O:15]1[CH:16]=[N:17][N:18]=[C:14]1[C:11]1[CH:12]=[CH:13][C:8]([O:7][C:6]2[CH:19]=[CH:20][C:3]([OH:2])=[CH:4][CH:5]=2)=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 2-[4-(4-Methoxy-phenoxy)-phenyl]-[1,3,4]oxadiazole (1.1 g, 4.1 mmol), methionine (0.94 g, 4.9 mmol) and methanesulfonic acid (20.5 mL) was heated to 50° C. for 1.5 hours. The mixture was poured into ice cold 5M sodium hydroxide solution (60 mL), diluted with sodium bicarbonate solution (saturated aqueous), and was extracted three times into ethyl acetate. The combined organic phases were dried over sodium sulfate (Na2SO4), filtered and concentrated in vacuo, affording 4-(4-[1,3,4]oxadiazol-2-yl-phenoxy)-phenol as a colorless solid (0.91 g).

Workup

extractionwas extracted three times into ethyl acetate
dry with materialThe combined organic phases were dried over sodium sulfate (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-0d42d15a12cb4d7cabd141e5b7258afd
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06706723B2

Linked notes

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