4-(2-Cyclopropylethoxy)-N-((Z)-2-(4-cyclopropylphenyl)-1-{[(2-hydroxyethyl)amino]carbonyl}vinyl)benzamide → N-{1-(4-Cyclopropylbenzyl)-2-[(2-hydroxyethyl)amino]-2-oxoethyl}-4-(2-cyclopropylethoxy)benzamide

HRID 1799232Notes

Reaction equation

[CH:1]1([CH2:4][CH2:5][O:6][C:7]2[CH:32]=[CH:31][C:10]([C:11]([NH:13]/[C:14](/[C:25]([NH:27][CH2:28][CH2:29][OH:30])=[O:26])=[CH:15]\[C:16]3[CH:21]=[CH:20][C:19]([CH:22]4[CH2:24][CH2:23]4)=[CH:18][CH:17]=3)=[O:12])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh].C(O)C.C1COCC1>[CH:22]1([C:19]2[CH:20]=[CH:21][C:16]([CH2:15][CH:14]([NH:13][C:11](=[O:12])[C:10]3[CH:9]=[CH:8][C:7]([O:6][CH2:5][CH2:4][CH:1]4[CH2:2][CH2:3]4)=[CH:32][CH:31]=3)[C:25]([NH:27][CH2:28][CH2:29][OH:30])=[O:26])=[CH:17][CH:18]=2)[CH2:23][CH2:24]1

Participants

Conditions

Temperature: 60 °C

Procedure

To an ethanol:THF (4:1, V/V, 7.5 mL) solution of 4-(2-cyclopropylethoxy)-N-((Z)-2-(4-cyclopropylphenyl)-1-{[(2-hydroxyethyl)amino]carbonyl}vinyl)benzamide (165 mg, 0.380 mmol) prepared in Example 1 (1d) was added tris(triphenylphosphine)rhodium(I) chloride (71 mg, 0.076 mmol). The mixture was stirred under a hydrogen atmosphere (rubber balloon) at 60° C. for 5 hours. The reaction solution was cooled to room temperature, and the solvent was evaporated. The residue was purified by alumina column chromatography (ethyl acetate to ethyl acetate:methanol, 10:1, V/V) to give 89 mg of the title compound (white powder, yield: 54%).

Workup

temperatureThe reaction solution was cooled to room temperature
customthe solvent was evaporated
customThe residue was purified by alumina column chromatography (ethyl acetate to ethyl acetate:methanol, 10:1, V/V)

Sources & evidence

ORD record: ord-7b2d9d1ed200473d99c3523751bd5972
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08344029B2

Reaction notes

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