HCID 22019641, compound → N-(3-cycloheptylphenyl)-3-methoxy-4-(2-phthalimidoethoxy)phenylacetamide

HRID 7071Notes

Reaction equation

FC1C(O[C:9](=[O:33])[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][N:20]3[C:24](=[O:25])[C:23]4=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]4[C:21]3=[O:30])=[C:13]([O:31][CH3:32])[CH:12]=2)=C(F)C(F)=C(F)C=1F.[CH:38]1([C:45]2[CH:46]=[C:47]([CH:49]=[CH:50][CH:51]=2)[NH2:48])[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1>C(OCC)(=O)C>[CH:38]1([C:45]2[CH:46]=[C:47]([NH:48][C:9](=[O:33])[CH2:10][C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][N:20]4[C:24](=[O:25])[C:23]5=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]5[C:21]4=[O:30])=[C:13]([O:31][CH3:32])[CH:12]=3)[CH:49]=[CH:50][CH:51]=2)[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]1

Participants

Conditions

Temperature: 60 °C

Procedure

3-Methoxy-4-(2-phthalimidoethoxy)phenylacetic acid pentafluorophenyl ester (690 mg) and 3-cycloheptylaniline (500 mg) are dissolved in ethyl acetate (10 ml), and the mixture is heated with stirring at 60° C. for 18 hours. The solvent is evaporated under reduced pressure, and the residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate) to give N-(3-cycloheptylphenyl)-3-methoxy-4-(2-phthalimidoethoxy)phenylacetamide (500 mg). This product is dissolved in ethanol (10 ml), and thereto is added hydrazine monohydrate (610 mg), and the mixture is heated under reflux for 2 hours. The insoluble materials are removed by filtration, and the solvent is evaporated under reduced pressure. To the residue is added water, and the mixture is extracted with chloroform. The organic layer is dried over sodium sulfate, and the residue is purified by silica gel column chromatography (eluent: gradient from 0% to 30% chloroform/methanol), and treated with 10% hydrogen chloride-methanol to give the desired compound (170 mg).

Workup

temperaturethe mixture is heated
customThe solvent is evaporated under reduced pressure
customthe residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate)

Sources & evidence

ORD record: ord-69c53f74268e4117b13f9b2679b14f4c
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07084176B2

Reaction notes

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