Hydroxyamine hydrochloride → HCID 9879458, compound

HRID 1362569Notes

Reaction equation

HRID 1362569 reaction equation
C[O-].[Na+].Cl.[NH2:5][OH:6].C[O:8][C:9](=O)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:27])/[CH:17]=[CH:18]/[CH:19]=[CH:20]/[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CO>[OH:6][NH:5][C:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:27])/[CH:17]=[CH:18]/[CH:19]=[CH:20]/[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:8]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 42599944HCID 42599944, compound

Product 1

HCID 9879458HCID 9879458, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

(Method J1B) A solution of sodium methylate (6 mmol) in methanol (5 ml) was added to a solution of hydroxylamine hydrochloride (0.28 g, 4 mmol) in methanol (8 ml). A mixture was stirred for 10 min. and the precipitate was filtered off. (2E)(4E)-6-(5-Phenylpenta-2,4-dienoylamino)hexanoic acid methyl ester (3/1) (0.30 g, 1 mmol) was added to the filtrate and the mixture was heated to the complete dissolving. The resultant mixture was stirred for 4 hours at ambient temperature and the solvent was removed under reduced pressure. The product was dissolved in water (10 ml) and acidified with 3% HCl. Precipitate was filtered off and crystallized from methanol. The title compound (0.23 g, 66%) was obtained as a white solid. M.p 160-161° C. 1H NMR (DMSO-d6, HMDSO), δ: 1.05-1.69 (6H, m, CH2); 1.81-2.07 (2H, m, CH2); 3.12 (2H, q, J=5.8 Hz, CH2H); 6.14 (1H, d, J=14.8 Hz, CH); 6.89-7.14 (2H, m, CH—CH); 7.23-7.65 (6H, m, C6H5, CH); 8.05 (1H, t, J=6.0 Hz, NH); 8.63 (1H, s, NH), 10.34 (1H, s, OH). HPLC analysis on Symmetry C18: impurities 1.0% (column size 3.9×150 mm; mobile phase acetonitrile −0.1 M phosphate buffer (pH 2.5), 30:70; detector UV 230 nm; sample concentration 0.1 mg/ml). Anal. Calcd for C17H22N2O3: C, 65.68; H, 6.61; N, 10.21. Found: C, 65.63; H, 6.60; N, 10.17.

Workup

  1. filtrationthe precipitate was filtered off
  2. temperaturethe mixture was heated to the complete dissolving
  3. customthe solvent was removed under reduced pressure
  4. dissolutionThe product was dissolved in water (10 ml)
  5. filtrationPrecipitate was filtered off
  6. customcrystallized from methanol

Sources & evidence

ORD record
ord-58807dba459a4f2ea0a60287895e5a6d
Source dataset
uspto-grants-2011_02
Patent number
US07880020B2

Reaction notes

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