3,3-Dimethylbutanal → Neotame

HRID 1421632Notes

Reaction equation

HRID 1421632 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]([NH:13][C:14]([C@@H:16]([NH2:21])[CH2:17][C:18]([OH:20])=[O:19])=[O:15])[CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:4].[CH3:22][C:23]([CH3:28])([CH3:27])[CH2:24][CH:25]=O.[H][H]>>[CH3:22][C:23]([CH2:24][CH2:25][NH:21][C@H:16]([C:14]([NH:13][C@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:15])[CH2:17][C:18]([OH:20])=[O:19])([CH3:28])[CH3:27]

Participants

4

Reactant 3

HCID 763353,3-DimethylbutanalHCID 134601AspartameHCID 178418361HCID 178418361, compound

Product 1

HCID 9810996Neotame

Procedure

U.S. Pat. No. 5,728,862 describes a method comprising treating a solution of aspartame and 3,3-dimethylbutyraldehyde in an organic solvent with the reducing agent, hydrogen in the presence of a catalyst. After removal of the catalyst, water is added to form an aqueous/organic solvent solution containing about 17% to about 30% of the organic solvent, by weight, from which the neotame is obtained by precipitation and filtration.

Workup

  1. customAfter removal of the catalyst, water
  2. additionis added
  3. customto form an aqueous/organic solvent solution

Sources & evidence

ORD record
ord-770111b6107248c1aeb9ef19b3c66b27
Source dataset
uspto-grants-2000_06
Patent number
US06077962

Reaction notes

Loading…