O-cyclohexylhydroxylamine hydrochloride → HCID 87416797, compound

HRID 600960Notes

Reaction equation

HRID 600960 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.Cl.[CH:19]1([O:25][NH2:26])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]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:26]/[O:25][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 18983924O-cyclohexylhydroxylamine hydrochlorideHCID 67482571(3-Chloro-4-methanesulfonyl-phenyl)-oxo-acetic acid methyl ester

Product 1

HCID 87416797HCID 87416797, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

(3-Chloro-4-methanesulfonyl-phenyl)-oxo-acetic acid methyl ester (prepared as in Example 1, 1.2 g, 4.34 mmol) was stirred in methanol (9 mL) and warmed in a 70° C. oil bath. O-Cyclohexyl-hydroxylamine hydrochloride (0.811 g, 5.43 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 μm; 20% ethyl acetate/hexanes to 50% ethyl acetate/hexanes) afforded (E)-(3-chloro-4-methanesulfonyl-phenyl)-cyclohexyloxyimino-acetic acid methyl ester as a white solid (552 mg, 34%): H1-NMR (400 MHz, CDCl3) δ=1.34 (3H, m), 1.51 (3H, m), 1.68 (2H, m), 1.96 (2H, m), 3.31 (3H, s), 3.91 (3H, s), 4.39 (1H, m), 7.51 (1H, dd, J=8.1 Hz, J=1.5 Hz), 7.62 (1H, d, J=1.5 Hz), 8.18 (1H, d, J=8.1 Hz).

Workup

  1. temperatureto cool
  2. concentrationconcentrated in vacuo
  3. customPurification by flash column chromatography (Merck silica gel 60, 40-63 μm; 20% ethyl acetate/hexanes to 50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-0a4e834d403948c98eb559e7579cb497
Source dataset
uspto-grants-2011_03
Patent number
US07902248B2

Reaction notes

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