Triethylamine → beta-Aspartylhydroxamic acid

HRID 724996Notes

Reaction equation

HRID 724996 reaction equation
CC[O:3][C:4](=[O:11])[C@@H:5]([CH2:7][C:8](O)=[O:9])[NH2:6].Cl.[NH2:13][OH:14].C(N(CC)CC)C>CO>[CH2:7]([C:8]([NH:13][OH:14])=[O:9])[CH:5]([NH2:6])[C:4]([OH:3])=[O:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 45082394(r)-Aspartic acid ethyl ester

Product 1

HCID 65274beta-Aspartylhydroxamic acidYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.1 mole of D-aspartic acid β-ethyl ester is dissolved in 200 ml of methanol, 0.2 mole of hydroxylamine hydrochloride is then added and the mixture is stirred until complete dissolution occurs. 0.4 mole of triethylamine is added and stirring is continued at room temperature for about 48 hr. The precipitate formed is collected on a filter. This crude product is recrystallized by dissolution in water, then diluted in absolute ethanol. This solution is kept at +4° C. for 12 hr. The crystals are filtered, washed with absolute ethanol and air-dried. This reaction yields 50 to 70% of D-Aspartic acid β-Hydroxamate.

Workup

  1. stirringstirring
  2. customThe precipitate formed
  3. customis collected on a filter
  4. customThis crude product is recrystallized by dissolution in water
  5. additiondiluted in absolute ethanol
  6. waitThis solution is kept at +4° C. for 12 hr
  7. filtrationThe crystals are filtered
  8. washwashed with absolute ethanol
  9. customair-dried

Sources & evidence

ORD record
ord-c18d97934711455681497800186e623a
Source dataset
uspto-grants-1998_01
Patent number
US05705522

Reaction notes

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