Ammonium Acetate → Methyl 3-amino-2-chloro-2-pentenoate

HRID 259798Notes

Reaction equation

HRID 259798 reaction equation
[Cl:1][CH:2]([C:7](=O)[CH2:8][CH3:9])[C:3]([O:5][CH3:6])=[O:4].C([O-])(=O)C.[NH4+:15]>CO>[NH2:15][C:7]([CH2:8][CH3:9])=[C:2]([Cl:1])[C:3]([O:5][CH3:6])=[O:4]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 545096Methyl 2-chloro-3-oxopentanoate

Product 1

HCID 86749529Methyl 3-amino-2-chloro-2-pentenoateYield 94.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 576.1 g (3.5 mol) of methyl 2-chloro-3-oxovalerate and 674.5 g (8.75 mol) of ammonium acetate in 1.2 l of methanol is heated at 65° C. with stirring for a period of 4 h. After cooling, the solvent is removed in vacuo, the residue is taken up in 2.5 l of diisopropyl ether, and the solid is removed. The solid is dissolved in a little water and subsequently extracted with ethyl acetate. The organic fractions are combined, dried over MgSO4 and evaporated in vacuo. Yield: 94.7% [GC]

Workup

  1. temperatureAfter cooling
  2. customthe solvent is removed in vacuo
  3. customthe solid is removed
  4. dissolutionThe solid is dissolved in a little water
  5. extractionsubsequently extracted with ethyl acetate
  6. dry with materialdried over MgSO4
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-8ada027996944489b3a4f6f695c30508
Source dataset
uspto-grants-1996_06
Patent number
US05523404

Reaction notes

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