Methanol → HCID 22990115, compound
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[O:17][CH2:16][CH2:15][C:14](C(O)=O)=[CH:13][C:12]=3[CH:21]=2)=[CH:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])C=CC=CC=1.C([N:41]([CH2:44]C)CC)C.[CH3:46][OH:47]>>[CH3:46][O:47][C:44]([NH:41][C:14]1[CH2:15][CH2:16][O:17][C:11]2[CH:10]=[CH:9][C:8]([C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=3)=[CH:21][C:12]=2[CH:13]=1)=[O:29]Participants
Procedure
A mixture of 7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine-4-carboxylic acid (561 mg), diphenylphosphoryl azide (0.43 ml), triethylamine (0.28 ml) and methanol (10 ml) was refluxed for 5 hours. The reaction mixture was evaporated to remove the solvent and was then extracted with ethyl acetate. The extract was washed successively with a 5% aqueous solution of citric acid, water, an aqueous solution of sodium bicarbonate, water and an aqueous solution of sodium chloride, was dried (anhydrous magnesium sulfate) and was then concentrated under reduced pressure. The residue was subjected to purification using silica gel column chromatography (ethyl acetate/hexane=1/4) to obtain 4-methoxycarbonylamino-7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine (180 mg) as a light yellow solid.
Workup
- temperaturewas refluxed for 5 hours
- customThe reaction mixture was evaporated
- customto remove the solvent
- extractionwas then extracted with ethyl acetate
- washThe extract was washed successively with a 5% aqueous solution of citric acid, water
- dry with materialan aqueous solution of sodium bicarbonate, water and an aqueous solution of sodium chloride, was dried (anhydrous magnesium sulfate)
- concentrationwas then concentrated under reduced pressure
- customThe residue was subjected to purification
Sources & evidence
- ORD record
- ord-8813d96d55d64c53a345dc410fb7a3ef
- Source dataset
- uspto-grants-2003_09
- Patent number
- US06627651B1
Reaction notes
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