Hydroxyamine hydrochloride → HCID 86746786, compound

HRID 247861Notes

Reaction equation

HRID 247861 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[C:5]1[CH:10]=[CH:9][C:8]([NH:11]C=O)=[C:7]([C:14](=O)[CH2:15][CH2:16][NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:6]=1)[CH3:2].Cl.[NH2:28][OH:29]>N1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:26])[C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[C:7]([C:14](=[N:28][OH:29])[CH2:15][CH2:16][NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:6]=1)[CH3:2]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 19764690HCID 19764690, compound

Product 1

HCID 86746786HCID 86746786, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of ethyl-4-formylamino-3-[3'-(N-tert-butyloxycarbonylamino)propionyl]benzoate (7.04 g, 20 mmol) and hydroxylamine hydrochloride (7.65 g, 110 mmol) in pyridine (200 ml), was heated at reflux for 15 hours. After this time the solution was cooled to ambient temperature and the solvent evaporated in vacuo. The residue was chromatographed (eluent 1:1 petrol:ethyl acetate) to give the title oxime (5.0 g, 71%) as a solid. m.p. 138°-140° C. NMR δ (250 MHz, CDCl3) 1.40 (12H, m), 3.13 (2H, t, J=7 Hz), 3.40 (2H, m), 4.31 (2H, q, J=7 Hz), 5.19 (1H, br s), 6.11 (2H, br s), 6.66 (1H, d, J=9 Hz), 7.73 (1H, dd, J=9 and 2 Hz), 8.10 (1H, br s), 10.46 (1H, br s).

Workup

  1. temperatureat reflux for 15 hours
  2. customthe solvent evaporated in vacuo
  3. customThe residue was chromatographed (eluent 1:1 petrol:ethyl acetate)

Sources & evidence

ORD record
ord-6bcbeb11716c493a8214dbd2acb11296
Source dataset
uspto-grants-1993_05
Patent number
US05208248

Reaction notes

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