HCID 10313222, compound → HCID 86663284, compound

HRID 1038319Notes

Reaction equation

HRID 1038319 reaction equation
[OH:1][CH2:2][C:3]([CH2:9][OH:10])([CH2:7][OH:8])[C:4]([OH:6])=[O:5].[N+](=[CH2:13])=[N-].C(OCC)C>CO>[OH:1][CH2:2][C:3]([CH2:9][OH:10])([CH2:7][OH:8])[C:4]([O:6][CH3:13])=[O:5]

Participants

4

Reactant 2

HCID 10313222HCID 10313222, compoundHCID 21186548Diazomethane diethylether

Product 1

HCID 86663284HCID 86663284, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 3-hydroxy-2,2-bis(hydroxymethyl)propanoic acid, prepared according to EP 751223 A2, in MeOH at rt is added dropwise 2 M trimethylsilyl)diazomethane/diethyl ether (1-5 equivalents) and the mixture is stirred at rt until the reaction is substantially complete as monitored by LCMS or TLC. The mixture is concentrated under reduced pressure and the residue is partitioned between saturated aq sodium bicarbonate solution and dichloromethane. The organic layer is separated, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue is purified by silica gel flash chromatography to afford methyl 3-hydroxy-2,2-bis(hydroxymethyl)propanoate.

Workup

  1. concentrationThe mixture is concentrated under reduced pressure
  2. customthe residue is partitioned between saturated aq sodium bicarbonate solution and dichloromethane
  3. customThe organic layer is separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-cdf3549152b2450a93de49df2c90694a
Source dataset
uspto-grants-2013_10
Patent number
US08551963B2

Reaction notes

Loading…