Ethylene Oxide → HCID 57247014, compound

HRID 1277685Notes

Reaction equation

HRID 1277685 reaction equation
[C:1]([NH:9][CH2:10][C:11]1([CH2:20][OH:21])[CH:16]([OH:17])[CH:15]([OH:18])[CH:14]([OH:19])[CH2:13][NH:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:22]1[O:24][CH2:23]1>O.C(O)(=O)C>[OH:24][CH2:23][CH2:22][N:12]1[CH2:13][CH:14]([OH:19])[CH:15]([OH:18])[CH:16]([OH:17])[C:11]1([CH2:10][NH:9][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:20][OH:21]

Participants

5

Reactant 2

HCID 6354Ethylene OxideHCID 23453189HCID 23453189, compound

Product 1

HCID 57247014HCID 57247014, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 962WaterSolvent

Procedure

4.44 g of 2-benzoylaminomethyl-2-hydroxymethyl-3,4,5-trihydroxypiperidine (Preparation example 3) are dissolved in 65 ml of water and, after adding one drop of acetic acid, 6 ml of ethylene oxide are added at about 5° C. After stirring the mixture for 24 hours, the reaction has ended. The mixture is concentrated, the residue is dissolved in about 40 ml of methanol/water 2:1 and the solution is discharged onto a column 20 cm long and 3 cm wide which contains Amberlite® IR 120, H+ form. The column is washed thoroughly with methanol/water 2:1 and then eluted with 0.1% strength ammonia. The individual fractions are investigated by thin layer chromatography to determine their content and the fractions containing the desired product are concentrated. 2.4 g of N-hydroxyethyl-2-benzoylaminomethyl-2-hydroxymethyl-3,4,5-trihydroxypiperidine are obtained in the form of a solid foam.

Workup

  1. additionare added at about 5° C
  2. concentrationThe mixture is concentrated
  3. dissolutionthe residue is dissolved in about 40 ml of methanol/water 2:1
  4. washThe column is washed thoroughly with methanol/water 2:1
  5. washeluted with 0.1% strength ammonia
  6. additionthe fractions containing the desired product
  7. concentrationare concentrated

Sources & evidence

ORD record
ord-8a1018d212e24468bdcaf6d3834916e9
Source dataset
uspto-grants-1981_07
Patent number
US04278683

Reaction notes

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