Hydrochloric Acid → Miglustat

HRID 2403066Notes

Reaction equation

HRID 2403066 reaction equation
[CH2:1]([N:5]1[C@H:34]([CH2:35][O:36]CC2C=CC=CC=2)[C@@H:25]([O:26]CC2C=CC=CC=2)[C@H:16]([O:17]CC2C=CC=CC=2)[C@@H:7]([O:8]CC2C=CC=CC=2)[CH2:6]1)[CH2:2][CH2:3][CH3:4].Cl.C1C=C2C(C(O)(O)C(=O)C2=CC=1)=O>CO.O.[Pd]>[CH3:4][CH2:3][CH2:2][CH2:1][N:5]1[C@H:34]([CH2:35][OH:36])[C@@H:25]([OH:26])[C@H:16]([OH:17])[C@@H:7]([OH:8])[CH2:6]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 10236NinhydrinHCID 10995459227932-82-32×

Product 1

HCID 51634Miglustat

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution obtained by mixing N-butyl 2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol of formula (III), obtained as in Example 2 (105.1 g, 0.17 mol) in methanol (500 mL) in the presence of 32% HCl (43.5 g), is treated with 16% Pd/C (10.2 g). The mixture is maintained under vigorous stirring under hydrogen atmosphere at 4 bars for about 4 hours, and then filtered through a perlite panel, and the solution obtained is concentrated at low pressure. The solid residue thus obtained is dissolved in water (100 mL), and the acid solution obtained is passed through a column on an ion-exchange resin activated in basic form (Amberlite IRA 900Cl). The fractions that tested positive to the ninhydrin assay were combined and concentrated at low pressure, obtaining 50 g of miglustat as an oily residue, having a chemical purity exceeding 98%, calculated by HPLC.

Workup

  1. customA solution obtained
  2. temperatureThe mixture is maintained
  3. filtrationfiltered through a perlite panel
  4. customthe solution obtained
  5. concentrationis concentrated at low pressure
  6. customThe solid residue thus obtained
  7. customthe acid solution obtained
  8. concentrationconcentrated at low pressure

Sources & evidence

ORD record
ord-835426db12af486ba674792c4f6fcab4
Source dataset
uspto-grants-2014_08
Patent number
US08802155B1

Reaction notes

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