Hydrochloric Acid → HCID 13059389, compound

HRID 325337Notes

Reaction equation

HRID 325337 reaction equation
[OH-:1].[K+].Cl.[NH2:4]O.C[O:7][C:8](=O)[C@H:9]([CH2:14][S:15][CH3:16])[NH:10][C:11](=[O:13])[CH3:12].Cl>CO.C(Cl)(Cl)Cl.C(OCC)(=O)C>[CH3:16][S:15][CH2:14][C@@H:9]([C:8]([NH:4][OH:1])=[O:7])[NH:10][C:11](=[O:13])[CH3:12]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 13059384HCID 13059384, compound

Product 1

HCID 13059389HCID 13059389, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent4×HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.32 g (20 mmole) of potassium hydroxide (85%) in 15 ml of methanol was added dropwise to a solution of 832 mg (12 mmole) of hydroxylamine hydrochloride in 20 ml of methanol under ice cooling sufficient to keep the temperature at +9° to +10° C. Similarly under ice cooling, a solution of 1.91 g (10 mmole) of S-methyl-N-acetyl-L-cysteine methyl ester in 15 ml of methanol was added dropwise. After completion of the dropwise addition, the temperature was allowed to rise to room temperature and the mixture was allowed to stand for 3 days as it was. Thereafter ethyl acetate which contained hydrogen chloride gas was added to attain a pH of about 4. The resulting precipitate was filtered off and the filtrate was concentrated in vacuo by distilling off the methanol. The residue thus obtained was subjected to chromatography on silica gel column (developing solvent: 10% methanol-containing chloroform) to give 1.68 g (88% yield) of N-(S-methyl-N-acetylcysteinyl)-hydroxylamine.

Workup

  1. customat +9° to +10° C
  2. additionAfter completion of the dropwise addition
  3. customto rise to room temperature
  4. additionwas added
  5. filtrationThe resulting precipitate was filtered off
  6. concentrationthe filtrate was concentrated in vacuo
  7. distillationby distilling off the methanol
  8. customThe residue thus obtained

Sources & evidence

ORD record
ord-57e39ba933e3426da690e093dd18391b
Source dataset
uspto-grants-1984_04
Patent number
US04440788

Reaction notes

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