Ammonia → Methyl 4-aminocarbonylbutyrate

HRID 970394Notes

Reaction equation

HRID 970394 reaction equation
[NH3:1].Cl[C:3]([CH2:5][CH2:6][CH2:7][C:8]([O:10][CH3:11])=[O:9])=[O:4]>C1COCC1>[NH2:1][C:3]([CH2:5][CH2:6][CH2:7][C:8]([O:10][CH3:11])=[O:9])=[O:4]

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 73916Methyl 4-chloroformylbutyrate

Product 1

HCID 11708070Methyl 4-aminocarbonylbutyrate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6.1 Ammonia is passed into 350 ml of cold THF for 30 minutes. 30 g of methyl 4-chlorocarbonylbutyrate are then added dropwise, with ammonia continuing to be passed in at the same time. The crystals which deposit are separated off, and the residue is boiled a number of times with ethyl acetate. The combined filtrates are distilled off, and the residue is recrystallised from ethyl acetate, giving 23.4 g of methyl 4-aminocarbonylbutyrate (“FA”), m.p. 80°.

Workup

  1. customThe crystals which deposit are separated off
  2. distillationThe combined filtrates are distilled off
  3. customthe residue is recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-9df2e34e32d04bf3a2dfc678437a4a58
Source dataset
uspto-grants-2007_12
Patent number
US07312224B2

Reaction notes

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