Hydroxylamine HCl → HCID 137195736, compound

HRID 242392Notes

Reaction equation

[Si:1]([O:18][CH2:19][C:20]1[N:24]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:23]([C:33](=O)[CH3:34])=[N:22][CH:21]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[OH:37][NH3+:38].C([O-])(=O)C.[Na+]>CO>[Si:1]([O:18][CH2:19][C:20]1[N:24]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:31])([CH3:32])[CH3:30])[C:23]([C:33](=[N:38][OH:37])[CH3:34])=[N:22][CH:21]=1)([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

1-[5-(tert-Butyldiphenylsilyloxymethyl)-1-(2-trimethylsilylethoxymethyl)-1H-imidazol-2-yl]ethanone (60.0 g) was dissolved in methanol (600 mL), and at room temperature hydroxylammonium chloride (16.4 g) and sodium acetate (24.2 g) were added, which mixture was subsequently warmed at 50° C., followed by stirring for 7 hours. After the reaction solution was cooled to room temperature, the insolubles were removed by filtration, and the mother liquor was concentrated to obtain the residue, which was purified by flash chromatography (ethyl acetate/hexane=10%→60%) using silica gel column (product name: Hi-Flash Column 5 L, manufactured by Yamazen Corporation) to afford the title compound (13.5 g).

Workup

temperatureAfter the reaction solution was cooled to room temperature
customthe insolubles were removed by filtration
concentrationthe mother liquor was concentrated
customto obtain the residue, which
customwas purified by flash chromatography (ethyl acetate/hexane=10%→60%)

Sources & evidence

ORD record: ord-27583e3e95044040a5907e05896903b7
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653126B2

Reaction notes

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