HCID 66953250, compound → HCID 86651326, compound

HRID 390078Notes

Reaction equation

HRID 390078 reaction equation
[OH:1][CH2:2][C@@H:3]1[C@@H:7]([CH2:8][S:9][CH3:10])[O:6]C(=O)[NH:4]1>CC(O)C.[OH-].[K+]>[NH2:4][C@@H:3]([C@H:7]([OH:6])[CH2:8][S:9][CH3:10])[CH2:2][OH:1]

Participants

4

Reactant 1

HCID 66953250HCID 66953250, compound

Product 1

HCID 86651326HCID 86651326, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 14797Potassium HydroxideSolvent

Conditions

Temperature
80 °C

Procedure

The product from Example 6.5 (1.16 g, 6.55 mmol) was dissolved in a mixture of iPrOH (32 ml) and 2M aq. KOH (14 ml) and stirred at 80° C. for 4 h. The solvent was evaporated and the residue chromatographed on silica gel (CH2Cl2-MeOH-28% aq. NH4OH, 9:1:0.1) to give (2R,3S)-2-amino-4-(methylthio)butane-1,3-diol (0.932 g, 94%) as a yellow solid.

Workup

  1. customThe solvent was evaporated
  2. customthe residue chromatographed on silica gel (CH2Cl2-MeOH-28% aq. NH4OH, 9:1:0.1)

Sources & evidence

ORD record
ord-7b7526eaddd4493bb96ce5d082aa815f
Source dataset
uspto-grants-2013_02
Patent number
US08383636B2

Reaction notes

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