Hydrochloric Acid → 5-Cyclopropyl-3-phenyl-isoxazole-4-carboxylic acid methoxy-methyl-amide

HRID 2219405Notes

Reaction equation

[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:5]=2[C:15]([OH:17])=O)[CH2:3][CH2:2]1.Cl.[CH3:19][NH:20][O:21][CH3:22].CN1CCOCC1.CN(C)CCCN=C=NCC.Cl>CN(C)C1C=CN=CC=1.ClCCl.CN(C=O)C>[CH3:22][O:21][N:20]([CH3:19])[C:15]([C:5]1[C:6]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[N:7][O:8][C:4]=1[CH:1]1[CH2:2][CH2:3]1)=[O:17]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 5-cyclopropyl-3-phenyl-isoxazole-4-carboxylic acid (3.72 g, 16 mmol), N,O-dimethylhydroxylamine hydrochloride (2.53 g, 26 mmol), N-methylmorpholine (2.85 mL, 26 mmol) and 4-dimethylaminopyridine (198 mg, 2 mmol) in dichloromethane (50 mL) and DMF (10 mL) was cooled to 0° C. Then 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (3.73 g, 19 mmol) was added and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was poured into hydrochloric acid (1 N) and extracted with ethyl acetate. The combined organic layers were then washed with a saturated solution of sodium hydrogen carbonate, brine and then dried over sodium sulphate and evaporated to leave a light yellow oil. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 50:50) afforded the title compound (4.03 g, 91%) which was obtained as a colourles oil. MS: m/e=273.0 [M+H]+.

Workup

extractionextracted with ethyl acetate
washThe combined organic layers were then washed with a saturated solution of sodium hydrogen carbonate, brine
dry with materialdried over sodium sulphate
customevaporated
customto leave a light yellow oil
customPurification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 50:50)

Sources & evidence

ORD record: ord-f7ed203a6e284f368d3910ba3e8cb754
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07414061B2

Reaction notes

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