Ammonia → tert-Butyl 3-amino-4-methylpent-2-enoate

HRID 704530Notes

Reaction equation

HRID 704530 reaction equation
[C:1]([CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])(=O)[CH:2]([CH3:4])[CH3:3].[NH3:14]>CO>[NH2:14][C:1]([CH:2]([CH3:4])[CH3:3])=[CH:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 10976205t-Butyl isobutyrylacetate

Product 1

HCID 71412665tert-Butyl 3-amino-4-methylpent-2-enoateYield 75.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Through a solution of 240 g of t-butyl isobutyrylacetate in 500 ml of methanol was passed 70 g of ammonia in 2 hours, maintaining the temperature at below 25° C. The resulting solution was stirred at room temperature for 18 hours, after which the methanol was removed in vacuo. Methylene chloride was added and the suspension was filtered. The filtrate was concentrated on a rotary evaporator to give 180 g t-butyl 3-amino-4-methyl-2-pentenoate as an oil.

Workup

  1. customin 2 hours
  2. temperaturemaintaining the temperature at below 25° C
  3. customafter which the methanol was removed in vacuo
  4. additionMethylene chloride was added
  5. filtrationthe suspension was filtered
  6. concentrationThe filtrate was concentrated on a rotary evaporator

Sources & evidence

ORD record
ord-02be5d7e581e43a1b1e370fafd1f90f2
Source dataset
uspto-grants-1991_01
Patent number
US04988384

Reaction notes

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