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

HRID 18836Notes

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, 2 H), 7.50-7.10 (m, 10 H), 7.00-6.70 (m, 2 H), 6.50-6.35 (m, 1 H), 5.30-5.00 (m, 2 H), 3.80 (d, 3 H); 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-3d68b527379643238794301cf5b8f912
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741493B2

Reaction notes

Loading…