Hydrochloric Acid → HCID 21340808, compound

HRID 1954056Notes

Reaction equation

HRID 1954056 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH:5]([N+:15]#[C-])[C:6]([CH3:14])([CH3:13])[C:7]([O:9][CH2:10][CH:11]=[CH2:12])=[O:8])[CH3:2].Cl.[OH-].[Na+]>CO>[CH2:1]([O:3][C:4](=[O:17])[CH:5]([NH2:15])[C:6]([CH3:14])([CH3:13])[C:7]([O:9][CH2:10][CH:11]=[CH2:12])=[O:8])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21340809HCID 21340809, compound

Product 1

HCID 21340808HCID 21340808, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

3-Isocyano-2,2-dimethyl-succinic acid 1-allyl ester 4-ethyl ester (3.75 g, 15.5 mmol) is dissolved in methanol (100 mL) and the mixture is cooled to 0° C. with an ice bath. To this is added, dropwise, 37% aqueous hydrochloric acid (1.58 g). The reaction is stirred 20 minutes and neutralized with 1 M aqueous sodium hydroxide. The volatiles are removed under vacuum and then the product is extracted into ethyl acetate (2x) and washed with water (2x). The combined organic phases are dried over sodium sulfate and evaporated to give 3-amino-2,2-dimethyl-succinic acid 1-allyl ester 4-ethyl ester as a yellow oil.

Workup

  1. additionTo this is added
  2. customThe volatiles are removed under vacuum
  3. extractionthe product is extracted into ethyl acetate (2x)
  4. washwashed with water (2x)
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-80b568e269ba468cace86bd866e346ac
Source dataset
uspto-grants-2000_09
Patent number
US06121258

Reaction notes

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