O-Cyclopentylhydroxylamine → HCID 87416800, compound

HRID 600944Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:17])[C:4]([C:6]1[CH:11]=[CH:10][C:9]([S:12]([CH3:15])(=[O:14])=[O:13])=[C:8]([Cl:16])[CH:7]=1)=O.[CH:18]1([O:23][NH2:24])[CH2:22][CH2:21][CH2:20][CH2:19]1>CO>[CH3:1][O:2][C:3](=[O:17])/[C:4](/[C:6]1[CH:11]=[CH:10][C:9]([S:12]([CH3:15])(=[O:14])=[O:13])=[C:8]([Cl:16])[CH:7]=1)=[N:24]/[O:23][CH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

Conditions

Temperature: 70 °C

Procedure

(3-Chloro-4-methanesulfonyl-phenyl)-oxo-acetic acid methyl ester (1.75 g, 6.32 mmol) was stirred in methanol (14 mL) and warmed in a 70° C. oil bath. O-Cyclopentyl-hydroxylamine (1.09 g, 7.92 mmol) was added. After 2 h, the reaction mixture was allowed to cool and concentrated in vacuo. Purification by flash column chromatography (Merck silica gel 60, 40-63 □m; 20% ethyl acetate/hexanes) gave (E)-(3-chloro-4-methanesulfonyl-phenyl)-cyclopentyloxyimino-acetic acid methyl ester (1.01 g, 44%) eluting second as a clear, colorless oil which solidified over time: H1-NMR (400 MHz, CDCl3) δ=1.62 (4H, m), 1.85 (4H, m), 3.31 (3H, s), 3.91 (3H, s), 4.96 (1H, m), 7.48 (1H, dd, J=8.2 Hz, J=1.3 Hz), 7.59 (1H, d, J=1.2 Hz), 8.17 (1H, d, J=8.2 Hz).

Workup

temperatureto cool
concentrationconcentrated in vacuo
customPurification by flash column chromatography (Merck silica gel 60, 40-63 □m; 20% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-a98dc981426c4a1b91d6113c06d9b777
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902248B2

Reaction notes

Loading…