4-Chlorobenzaldehyde → HCID 70024508, compound

HRID 1602093Notes

Reaction equation

HRID 1602093 reaction equation
[ClH:1].Cl.ON=C(N[CH2:8][CH2:9][CH2:10][CH2:11][C@@:12]([CH3:17])([C:14](O)=O)N)C.Cl.Cl.C([O:22][C:23](=[O:31])[C@H:24]([CH2:26][CH2:27][CH2:28][CH2:29][NH2:30])[NH2:25])C.[O-]S([O-])(=O)=O.[Mg+2].[Cl:38][C:39]1[CH:46]=[CH:45][C:42]([CH:43]=O)=[CH:41][CH:40]=1.C(N([CH2:54][CH3:55])C(C)C)(C)C>C(#N)C>[CH2:54]([C@@:24]([C:23]([OH:22])=[O:31])([CH2:26][CH2:27][CH2:28][CH2:29][N:30]=[CH:17][C:12]1[CH:14]=[CH:8][C:9]([Cl:1])=[CH:10][CH:11]=1)[N:25]=[CH:43][C:42]1[CH:45]=[CH:46][C:39]([Cl:38])=[CH:40][CH:41]=1)[CH3:55]

Participants

7

Reactant 5

HCID 77264-ChlorobenzaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 81531DiisopropylethylamineHCID 107468Lysine ethyl ester dihydrochlorideHCID 178465700HCID 178465700, compound

Product 1

HCID 70024508HCID 70024508, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N6-[1-(hydroxyimino)ethyl]-2-methyl-lysine, dihydrochloride ##STR8## EX-3A) A suspension of lysine ethyl ester dihydrochloride (33 g; 0.14 mole) and MgSO4 (34 g; 0.28 moles) in a solution of 4-chloro-benzaldehyde (39 g; 0.28 moles) and acetonitrile (500 mL) was stirred while N,N-diisopropylethylamine (36 g; 0.28 moles) was added in portions over 1/2 h. The mixture was stirred for 12 h, filtered, concentrated to a small volume, and diluted with 500 mL of diethyl ether. The ether solution was washed with 0.1% aqueous NaHCO3, aqueous 2 N NaOH containing 2 g/100 ml of NH2OH.HCl, again with 0.1% aqueous NaHCO3 and saturated aqueous NaCl. After drying with MgSO4 and removal of the solvent in vacuo, ethyl N, N'-di(4-chloro-phenylmethylene)-L-lysine was obtained as a clear liquid.

Workup

  1. additionwas added in portions over 1/2 h
  2. filtrationfiltered
  3. concentrationconcentrated to a small volume
  4. additiondiluted with 500 mL of diethyl ether
  5. washThe ether solution was washed with 0.1% aqueous NaHCO3, aqueous 2 N NaOH containing 2 g/100 ml of NH2OH.HCl, again with 0.1% aqueous NaHCO3 and saturated aqueous NaCl
  6. dry with materialAfter drying with MgSO4 and removal of the solvent in vacuo

Sources & evidence

ORD record
ord-8837ba519e45434084a79dce854a57ce
Source dataset
uspto-grants-1999_11
Patent number
US05981511

Reaction notes

Loading…