Sodium Hydroxide → 3-[N-(2,2,5,5-Tetramethyl-1,3-dioxane-4-carbonyl)amino]propionic acid

HRID 892874Notes

Reaction equation

HRID 892874 reaction equation
[OH-].[Na+].[CH3:3][C:4]1([CH3:27])[O:9][CH:8]([C:10]([NH:12][CH2:13][CH2:14][C:15]([O:17]CC2C=CC=CC=2)=[O:16])=[O:11])[C:7]([CH3:26])([CH3:25])[CH2:6][O:5]1>CO>[CH3:3][C:4]1([CH3:27])[O:9][CH:8]([C:10]([NH:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[O:11])[C:7]([CH3:26])([CH3:25])[CH2:6][O:5]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19893743benzyl 3-[N-(2,2,5,5-Tetramethyl-1,3-dioxane-4-carbonyl)amino]propionate

Product 1

HCID 189385173-[N-(2,2,5,5-Tetramethyl-1,3-dioxane-4-carbonyl)amino]propionic acidYield 78.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

An aqueous 1N sodium hydroxide solution (100 ml) was added to a solution 35 g of benzyl 3-[N-(2,2,5,5-Tetramethyl-1,3-dioxane-4-carbonyl)amino]propionate in 350 ml of methanol, and the mixture was stirred under ice cooling for 1 hour. After completion of the reaction, methanol was distilled off under reduced pressure. The aqueous layer was extracted with ethyl acetate. After adding 1N hydrochloric acid to the aqueous layer to render it acidic, the aqueous layer was extracted with ethyl acetate. The organic layer washed with water and then with saturated saline, and dried over anhydrous sodium sulfate. Removal of the solvent by evapoation afforded 20.4 g of the objective compound (yield: 78%).

Workup

  1. distillationwas distilled off under reduced pressure
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. additionAfter adding 1N hydrochloric acid to the aqueous layer
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe organic layer washed with water
  6. dry with materialwith saturated saline, and dried over anhydrous sodium sulfate
  7. customRemoval of the solvent by evapoation

Sources & evidence

ORD record
ord-83bd17a0a4814da8ab297587e8654464
Source dataset
uspto-grants-1992_06
Patent number
US05120738

Reaction notes

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