Hydroxyamine hydrochloride → HCID 9880118, compound

HRID 1062358Notes

Reaction equation

HRID 1062358 reaction equation
C[O-].[Na+].Cl.[NH2:5][OH:6].C[O:8][C:9](=O)[CH2:10][CH2:11][S: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][S: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 23399151HCID 23399151, compound

Product 1

HCID 9880118HCID 9880118, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

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. 3-{2-[(2E)(4E)-5-phenylpenta-2,4-dienoylamino]ethylsulfanyl}propionic acid methyl ester (3/28) (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. Yield 47%, m.p. 158-160° C. 1H NMR (90 MHz, DMSO-d6) δ: 2.24 (2H, t, J=6.8 Hz, CH2); 2.56-2.87 (4H, m, CH2); 3.29 (2H, q, J=6.0 Hz, CH2); 6.14 (1H, d, J=15.0 Hz, CH); 6.83-7.14 (2H, m, CH—CH); 7.14-7.66 (6H, m, C6H5, CH); 8.21 (1H, t, J=5.5 Hz, NH); 8.74 (1H, s, NH), 10.42 (1H, s, OH). HPLC analysis on Symmetry C18 column: impurities 2.6% (column size 3.9×150 mm; mobile phase acetonitrile—0.1M phosphate buffer (pH 2.5), 35:65; detector UV 230 nm; sample concentration 0.3 mg/ml). Anal. Calcd for C16H20N2O3S: C, 59.98; H, 6.29; N, 8.74. Found: C, 59.82; H, 6.23; N, 8.68.

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-c0ca6ba34f4b413891fdd1b54543c3f7
Source dataset
uspto-grants-2005_11
Patent number
US06960685B2

Reaction notes

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