Potassium Hydroxide → Boc-D-Glu-OH

HRID 1871208Notes

Reaction equation

HRID 1871208 reaction equation
[NH2:1][C@@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[OH:6].[OH-].[K+].[O:13](C(OC(C)(C)C)=O)[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=O>O.O1CCOCC1>[NH:1]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:13])[C@@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5](=[O:6])[OH:7]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 23327D-Glutamic AcidHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 7019046Boc-D-Glu-OH

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

14.7 g (0.1 Mol) of H-D-Glu-OH was dissolved in 200 ml of distilled water, and the pH was adjusted to 10.2 with 0.1M potassium hydroxide. 33.0 g (0.3 Mol) of BOC2O in dioxane was added with intensive mixing. The pH was controlled using a pH-stat. After completion of the reaction, the mixture was transferred to a separating funnel, and extraction was carried out from the alkaline solution with ethyl acetate (3×150 ml). The pH of the aqueous phase was adjusted to 3.0 using 0.2% sulphuric acid, and Boc-D-Glu-OH was extracted from the organic phase (3×200 ml). The organic phase was washed three times with 200 ml of Na2SO4 saturated solution to neutral pH, and dried over Na2SO4, and evaporated to oil under vacuum. The yield was 16.7 g (68%).

Workup

  1. customAfter completion of the reaction
  2. customthe mixture was transferred to a separating funnel
  3. extractionextraction
  4. extractionwas extracted from the organic phase (3×200 ml)
  5. washThe organic phase was washed three times with 200 ml of Na2SO4 saturated solution to neutral pH
  6. dry with materialdried over Na2SO4
  7. customevaporated to oil under vacuum

Sources & evidence

ORD record
ord-e7a16e7f14cf4e7fb80a2c8eadc4ccf9
Source dataset
uspto-grants-2000_08
Patent number
US06103699

Reaction notes

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