Sulfuric acid magnesium salt (1:1) → N-[2-(7-Isopropyl-2-methyl-6H-indeno[5,4-d][1,3]oxazol-8-yl)ethyl]acetamide

HRID 883265Notes

Reaction equation

O[C:2]1([CH2:18][CH2:19][NH:20][C:21](=[O:23])[CH3:22])[C:13]2[C:12]3[O:11][C:10]([CH3:14])=[N:9][C:8]=3[CH:7]=[CH:6][C:5]=2[CH2:4][CH:3]1[CH:15]([CH3:17])[CH3:16].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.S([O-])([O-])(=O)=O.[Mg+2]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH:15]([C:3]1[CH2:4][C:5]2[CH:6]=[CH:7][C:8]3[N:9]=[C:10]([CH3:14])[O:11][C:12]=3[C:13]=2[C:2]=1[CH2:18][CH2:19][NH:20][C:21](=[O:23])[CH3:22])([CH3:17])[CH3:16]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of N-[2-(8-hydroxy-7-isopropyl-2-methyl-7,8-dihydro-6H-indeno[5,4-d][1,3]oxazol-8-yl)ethyl]acetamide (132 mg, 0.417 mmol) in toluene (4.2 mL) were added p-toluenesulfonic acid monohydrate (396 mg, 2.08 mmol) and magnesium sulfate (1 g), and the mixture was stirred at 100° C. for 1 hr. The reaction solution was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane=30/70→100/0) to give the title compound (76.1 mg, yield 61%).

Workup

washwashed with saturated aqueous sodium hydrogencarbonate solution and saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane=30/70→100/0)

Sources & evidence

ORD record: ord-239e1d56e31847a0ad15c2d304f286b3
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236837B2

Reaction notes

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