Pyridine → (S)-[2-(Hydroxylimino)-2-(4-methoxyphenyl)-1-phenylethyl]carbamic Acid Benzyl Ester

HRID 2053627Notes

Reaction equation

[CH2:1]([O:8][C:9](=[O:28])[NH:10][C@@H:11]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:12]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:30][OH:31].N1C=CC=CC=1>CCO>[CH2:1]([O:8][C:9](=[O:28])[NH:10][C@@H:11]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:12](=[N:30][OH:31])[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of the ketone 483 (2.47 g, 6.6 mmol) in EtOH (35 mL) is added hydroxylamine hydrochloride (1.83 g, 26.4 mmol) followed by pyridine (2.13 mL, 26.4 mmol). The mixture is stirred at 80° C. for 8 h. The reaction mixture is cooled, the solvent is evaporated, and the residue dissolved in EtOAc, washed with water, brine, then dried (MgSO4), and filtered. The filtrate is evaporated, and the residue purified by chromatography on silica gel; elution with heptane:EtOAc (7:3) gives 1.95 g of the product 484. 1H NMR (CDCl3) δ 7.55 (d, 2H), 7.50-7.10 (m, 10H), 7.00-6.70 (m, 2H), 6.50-6.35 (m, 1H), 5.30-5.00 (m, 2H), 3.80 (d, 3H); MS: m/z 391 (M++1).

Workup

temperatureThe reaction mixture is cooled
customthe solvent is evaporated
dissolutionthe residue dissolved in EtOAc
washwashed with water, brine
dry with materialdried (MgSO4)
filtrationfiltered
customThe filtrate is evaporated
customthe residue purified by chromatography on silica gel
washelution with heptane:EtOAc (7:3)

Sources & evidence

ORD record: ord-ca28befc5a504b6abc8777c093cae9d9
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07326792B2

Reaction notes

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