3,3-Dimethylbutanal → Neotame

HRID 991954Notes

Reaction equation

HRID 991954 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 hydrogen in the presence of a catalyst as a reducing agent. After removal of the catalyst, water was added to form an aqueous/organic solvent solution containing about 17% to about 30% of the organic solvent, by weight, from which the neotame was obtained by precipitation and filtration.

Workup

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

Sources & evidence

ORD record
ord-943b229e42c04e61a106a0b8918d0fcd
Source dataset
uspto-grants-2002_10
Patent number
US06465677B1

Reaction notes

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