Hydroxyamine hydrochloride → 5-[(E)-N-hydroxy-C-[(2S)-2-(2-methylphenyl)-2-(4-methylsulfonylphenyl)ethyl]carbonimidoyl]-1-methylpyridin-2-one

HRID 1618047Notes

Reaction equation

[CH3:1][N:2]1[CH:7]=[C:6]([C:8](=O)[CH2:9][C@H:10]([C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[CH:5]=[CH:4][C:3]1=[O:29].Cl.[NH2:31][OH:32].C(=O)([O-])O.[Na+]>C(O)C.O.C(OCC)(=O)C>[OH:32]/[N:31]=[C:8](/[C:6]1[CH:5]=[CH:4][C:3](=[O:29])[N:2]([CH3:1])[CH:7]=1)\[CH2:9][C@@H:10]([C:18]1[CH:19]=[CH:20][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:22][CH:23]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17]

Participants

Conditions

Temperature: 120 °C

Procedure

To a microwave vial was added (R)-1-methyl-5-(3-(4-(methylsulfonyl)phenyl)-3-o-tolylpropanoyl)pyridin-2(1H)-one (168 mg, 410 μmol), hydroxylamine hydrochloride (85.5 mg, 1.23 mmol) and sodium hydrogencarbonate (103 mg, 1.23 mmol) in ethanol (3 mL) and water (0.2 mL). The vial was capped and heated at 120° C. for 15 min. The reaction mixture was diluted with ethyl acetate and poured onto water. The organic layer was washed with brine, dried over magnesium sulfate and evaporated to afforded the title compound (169 mg, 97%) as a mixture of the E and Z isomers (ratio ca. 85:15). Light yellow foam, MS (ESI+): m/z=425.2 [M+H]+.

Workup

customThe vial was capped
additionpoured onto water
washThe organic layer was washed with brine
dry with materialdried over magnesium sulfate
customevaporated

Sources & evidence

ORD record: ord-37218d95b1a447aeab1e6ed68df0e015
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765730B2

Reaction notes

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