Hydroxyamine hydrochloride → HCID 178436623, compound

HRID 1958776Notes

Reaction equation

HRID 1958776 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) was carefully dissolved in MeOH (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 MeOH (7.5 mL) was added. The mixture was refluxed for 8 h and the solvent was evaporated. The residue was dissolved in 2 N aq. HCl and extracted with EA. The pH of the aq. phase was adjusted to pH 5 by adding sat. aq. NaHCO3 and the mixture was extracted three times with EA. The combined org. extracts were dried over Na2SO4, filtered, evaporated and dried to give 3-[2-ethyl-4-(N-hydroxycarbamimidoyl)-6-methyl-phenyl]-propionic acid as a white solid (1.4 g). LC-MS: tR=0.60 min, [M+1]+=251.17.

Workup

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

Sources & evidence

ORD record
ord-caad55837826438e8368dedd04165c62
Source dataset
uspto-grants-2013_04
Patent number
US08410151B2

Reaction notes

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