Hydroxyamine hydrochloride → HCID 178436623, compound

HRID 1665920Notes

Reaction equation

HRID 1665920 reaction equation
CC(C)([O-])C.[K+].Cl.[NH2:8][OH:9].[C:10]([C:12]1[CH:17]=[C:16]([CH3:18])[C:15]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[C:14]([CH2:24][CH3:25])[CH:13]=1)#[N:11]>CO>[CH2:24]([C:14]1[CH:13]=[C:12]([C:10](=[NH:11])[NH:8][OH:9])[CH:17]=[C:16]([CH3:18])[C:15]=1[CH2:19][CH2:20][C:21]([OH:23])=[O:22])[CH3:25]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 23665647Potassium tert-butoxideHCID 574374143-(4-Cyano-2-ethyl-6-methylphenyl)propionic acid

Product 1

HCID 178436623HCID 178436623, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Potassium tert.butoxide (2.71 g, 24.1 mmol) is carefully dissolved in methanol (25 mL). To this solution hydroxylamine hydrochloride (1.44 g, 20.7 mmol) followed by 3-(4-cyano-2-ethyl-6-methyl-phenyl)-propionic acid (1.50 g, 6.90 mmol) dissolved in methanol (7.5 mL) is added. The mixture is refluxed for 8 h and the solvent is evaporated. The residue is dissolved in 2 N aq. HCl and extracted with EA. The pH of the aq. phase is adjusted to pH 5 by adding sat. aq. NaHCO3 and the mixture is extracted three times with EA. The combined organic extracts are dried over Na2SO4, filtered, evaporated and dried to give 3-[2-ethyl-4-(N-hydroxycarbamimidoyl)-6-methyl-phenyl]-propionic acid (1.4 g) as a white solid; LC-MS: tR=0.60 min, [M+1]+=251.17.

Workup

  1. additionis added
  2. temperatureThe mixture is refluxed for 8 h
  3. customthe solvent is evaporated
  4. dissolutionThe residue is dissolved in 2 N aq. HCl
  5. extractionextracted with EA
  6. additionby adding sat. aq. NaHCO3
  7. extractionthe mixture is extracted three times with EA
  8. dry with materialThe combined organic extracts are dried over Na2SO4
  9. filtrationfiltered
  10. customevaporated
  11. customdried

Sources & evidence

ORD record
ord-2996159b3b2841079b77fdd563614c01
Source dataset
uspto-grants-2011_10
Patent number
US08039644B2

Reaction notes

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