Hydrochloric Acid → HCID 54212775, compound

HRID 2351541Notes

Reaction equation

HRID 2351541 reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[O:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29])(=O)C.CO.C[O-].[Na+].Cl>O.C(Cl)(Cl)Cl>[C@@H:6]1([O:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29])[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]1[OH:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 10942334Sodium MethoxideHCID 11070107HCID 11070107, compound

Product 1

HCID 54212775HCID 54212775, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

1.5 g (3.4 mmol) of 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-butyric acid (see Stage 1.1) are taken up in 13 ml f chloroform and, at -10°, 22 ml of methanol containing 17.3 mmol of sodium methoxide (obtained by dissolving 400 mg of sodium) are added thereto. Stirring is carried out for 1 1/2 hours at 0° and for 1 hour at 22°. The mixture is cooled to 0°, 2 ml of water are added and the whole is adjusted to pH 3.0 with 1 molar hydrochloric acid. Concentration is carried out by evaporation in vacuo and the residue is taken up in warm ethanol and the resulting sodium chloride is filtered off. After concentrating the filtrate by evaporation, 4-(β-D-glucopyranosyloxy)butyric acid is obtained.

Workup

  1. temperatureThe mixture is cooled to 0°
  2. concentrationConcentration
  3. customis carried out by evaporation in vacuo
  4. filtrationthe resulting sodium chloride is filtered off
  5. concentrationAfter concentrating the filtrate
  6. customby evaporation

Sources & evidence

ORD record
ord-70a06fe57f444de8a706d12d9ee75d4c
Source dataset
uspto-grants-1989_10
Patent number
US04873322

Reaction notes

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