Hydrochloric Acid → HCID 21340808, compound

HRID 2184785Notes

Reaction equation

HRID 2184785 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 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 (2×) and washed with water (2×). 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 (2×)
  4. washwashed with water (2×)
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-42f3e21b70024287ad03192c05b0f530
Source dataset
uspto-grants-2002_06
Patent number
US06399598B1

Reaction notes

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