Hydroxylamine → HCID 67246026, compound

HRID 1027606Notes

Reaction equation

HRID 1027606 reaction equation
[OH-:1].[Na+].[NH2:3]O.[Cl:5][C:6]1[CH:7]=[C:8]([C:13]([C:35]([F:38])([F:37])[F:36])=[CH:14][C:15]([C:17]2[CH:33]=[CH:32][C:20]([C:21]([NH:23][C@@H:24]3[CH2:28][O:27][N:26]([CH2:29][CH3:30])[C:25]3=[O:31])=[O:22])=[C:19]([CH3:34])[CH:18]=2)=O)[CH:9]=[C:10]([Cl:12])[CH:11]=1>ClC(Cl)C.ClCCl>[Cl:5][C:6]1[CH:7]=[C:8]([C:13]2([C:35]([F:38])([F:37])[F:36])[O:1][N:3]=[C:15]([C:17]3[CH:33]=[CH:32][C:20]([C:21]([NH:23][CH:24]4[CH2:28][O:27][N:26]([CH2:29][CH3:30])[C:25]4=[O:31])=[O:22])=[C:19]([CH3:34])[CH:18]=3)[CH2:14]2)[CH:9]=[C:10]([Cl:12])[CH:11]=1

Participants

6

Reactant 3

HCID 787HydroxylamineHCID 14798Sodium HydroxideHCID 67246523HCID 67246523, compound

Product 1

HCID 67246026HCID 67246026, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
5 °C

Procedure

A pre-cooled solution of 5M sodium hydroxide (0.09 ml) was added to a solution of hydroxylamine (50% in water, 0.024 ml) at 5° C. (ice bath). The solution was stirred for 15 min at 5° C. then added to a vigorously stirred solution of 4-[3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-but-2-enoyl]-N-((R)-2-ethyl-3-oxo-isoxazolidin-4-yl)-2-methyl-benzamide (100 mg) and anthracenyl-methyl quininium bromide (20 mg) (Step A) in dichloroethane (1 ml) cooled in an ice-acetone bath. The mixture was stirred rapidly at 0° C. for 4 hours. The reaction mixture was diluted with dichloromethane, passed through an isolute phase separating cartridge and concentrated in vacuo to leave yellow oil. This residue was purified by chromatography on silica gel (eluent: heptane/ethyl acetate 5%) to give the title compound (9 mg). The product was analysed by chiral HPLC (method H): 18.7 min (42.5%), 19.6 min (24.2%), 21.4 min (8.5%), 22.8 min (24.8%).

Workup

  1. temperaturecooled in an ice-acetone bath
  2. stirringThe mixture was stirred rapidly at 0° C. for 4 hours
  3. customseparating cartridge
  4. concentrationconcentrated in vacuo
  5. customto leave yellow oil
  6. customThis residue was purified by chromatography on silica gel (eluent: heptane/ethyl acetate 5%)

Sources & evidence

ORD record
ord-a0fbce93c78d4dfbbd917e7678d43f76
Source dataset
uspto-grants-2014_05
Patent number
US08735362B2

Reaction notes

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