Hydrochloric Acid → N-acetyl-2-vinylglutamic acid

HRID 26034Notes

Reaction equation

HRID 26034 reaction equation
[CH:1]([C@@:3]([C:10]([OH:12])=[O:11])([CH2:5][CH2:6][C:7]([OH:9])=[O:8])[NH2:4])=[CH2:2].[C:13](Cl)(=[O:15])[CH3:14].Cl>[OH-].[Na+].O1CCOCC1>[C:13]([NH:4][C@:3]([CH:1]=[CH2:2])([C:10]([OH:12])=[O:11])[CH2:5][CH2:6][C:7]([OH:9])=[O:8])(=[O:15])[CH3:14]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 540919112-Vinylglutamic acid

Product 1

HCID 54293490N-acetyl-2-vinylglutamic acid

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-vinylglutamic acid (350 mg, 2 mM) in 5 ml of 1 N sodium hydroxide at 0° C. are added simultaneously from 2 syringes acetyl chloride (160 mg) diluted in dioxane (1 ml) and 2 ml of 1 N sodium hydroxide. After 30 minutes at 0° the solution is acidified by the addition of 3 N hydrochloric acid, then extracted well with dichloromethane. The organic phase is dried and concentrated to afford N-acetyl-2-vinylglutamic acid.

Workup

  1. extractionextracted well with dichloromethane
  2. customThe organic phase is dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1e1ea816bdb94a25a3ba646f8924e8db
Source dataset
uspto-grants-1979_04
Patent number
US04147873

Reaction notes

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