Hydrochloric Acid → alpha-Amino-3-oxo-5-isoxazolidineacetic acid

HRID 127793Notes

Reaction equation

HRID 127793 reaction equation
[NH2:1][C@@H:2]([C@H:6]1[O:10][N:9]=[C:8](Cl)[CH2:7]1)[C:3]([OH:5])=[O:4].[OH-:12].[Na+].Cl>>[CH2:7]1[C:8]([OH:12])=[N:9][O:10][CH:6]1[CH:2]([NH2:1])[C:3]([OH:5])=[O:4]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 294641Acivicin

Product 1

HCID 178511453alpha-Amino-3-oxo-5-isoxazolidineacetic acidYield 80%

Procedure

To 1.20 g. (6.75 mmole) of (αS,5S)-α-amino-3-chloro-4,5-dihydro-5-isoxazol-acetic acid (AT-125), is added 20 ml. of 2 N sodium hydroxide and stirred at 25° for 36 hours. The solution is brought to ~3.5 pH with 6 N hydrochloric acid (dropwise addition) and then stored at -10° (freezer) overnight. The crystals are collected by filtration, washed twice with cold water, and then dried giving 720 mg. of trichloromic acid. The initial filtrate is lyophilized and the resulting powder is taken up in 4 ml. of water, filtered, and washed with two 4 ml. portions of cold water, and dried yielding an extra 160 mg. of tricholomic acid (total 80% yield).

Workup

  1. additiondropwise addition) and
  2. customthen stored at -10°
  3. custom(freezer) overnight
  4. filtrationThe crystals are collected by filtration
  5. washwashed twice with cold water
  6. customdried
  7. customgiving 720 mg
  8. filtrationof water, filtered
  9. washwashed with two 4 ml
  10. dry with materialportions of cold water, and dried
  11. customyielding an extra 160 mg

Sources & evidence

ORD record
ord-51e8d2334c1441f4829069c3b99cec70
Source dataset
uspto-grants-1981_03
Patent number
US04256898

Reaction notes

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