Reaction #1378866

ord-cce74fd36e424e9694404c427e56d221

Reaction equation

O=C1CCCO1
gamma-butyrolactone
O=C(O)CCCO
gamma-hydroxybutyric acid
CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
methylglucamine
→
CCC(O)C(=O)O[C@@H]([C@H](O)[C@@H](O)CNC)[C@H](O)CO
1-desoxy-1-methylamino-D-glucitol 4-hydroxybutyrate

Reactants

O=C1CCCO1
gamma-butyrolactone
—
11
O=C(O)CCCO
gamma-hydroxybutyric acid
CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
methylglucamine

Reagents

None

Solvents

O
water
—
solution
O
water

Conditions

Temperature
60°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherobtained
  2. 2
    workup.WAITThe pH value falls over this period
  3. 3
    OtherThe volume of the solution obtained

Procedure

500 ml (565 g, 6.56 mol) of gamma-butyrolactone are placed in 1.8 l of water. 1.28 kg (6.56 mol) of methylglucamine are added to the solution obtained. The mixture is then heated to 60° C. for 8 hours. The pH value falls over this period from an initial value of 11 to 7.5. The volume of the solution obtained is then adjusted to 3.4 l by the addition of water (approximately 200 ml) in order to achieve a concentration of 2 g of gamma-hydroxybutyric acid in 10 ml of solution.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05753708uspto-grants-1998_05