Triethylamine → (2S,3R)-2-aminomethyl-3-hydroxybutyric acid

HRID 1090291Notes

Reaction equation

HRID 1090291 reaction equation
Cl.[NH2:2][CH2:3][C@@H:4]([C@H:8]([OH:10])[CH3:9])[C:5]([OH:7])=[O:6].C(N(CC)CC)C>C(#N)C>[NH2:2][CH2:3][C@@H:4]([C@H:8]([OH:10])[CH3:9])[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 86744465(2S,3R)-2-aminomethyl-3-hydroxybutyric acid hydrochloride

Product 1

HCID 10975521(2S,3R)-2-aminomethyl-3-hydroxybutyric acidYield 84.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6.14 g (36.22 mmol) of (2S,3R)-2-aminomethyl-3-hydroxybutyric acid hydrochloride was added with 150 ml of acetonitrile, and further added, while cooled in ice, with 5.05 ml (36.22 mmol) of triethylamine, then subjected to a vigorous stirring for 2 days at room temperature. Powdery crystals precipitated were collected, washed with 100 ml of acetonitrile and filtered to obtain 4.07 g of the title compound in crystals (yield: 84%).

Workup

  1. additionfurther added
  2. customPowdery crystals precipitated
  3. customwere collected
  4. washwashed with 100 ml of acetonitrile
  5. filtrationfiltered

Sources & evidence

ORD record
ord-dd9b4d82c77c415a9ab3d2610578799a
Source dataset
uspto-grants-1992_01
Patent number
US05081239

Reaction notes

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