3,3-Dimethylbutanal → Aspartame

HRID 1182394Notes

Reaction equation

HRID 1182394 reaction equation
[CH3:1][C:2]([CH2:5][CH2:6][NH:7][C@H:8]([C:13]([NH:15][C@H:16]([C:24]([O:26][CH3:27])=[O:25])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:14])[CH2:9][C:10]([OH:12])=[O:11])([CH3:4])[CH3:3].CC(C)(C)CC=O>>[CH3:27][O:26][C:24]([C@@H:16]([NH:15][C:13]([C@@H:8]([NH2:7])[CH2:9][C:10]([OH:12])=[O:11])=[O:14])[CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:25].[CH3:4][C:2]([CH2:5][CH2:6][NH:7][C@H:8]([C:13]([NH:15][C@H:16]([C:24]([O:26][CH3:27])=[O:25])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:14])[CH2:9][C:10]([OH:12])=[O:11])([CH3:1])[CH3:3]

Participants

4

Reactant 2

HCID 763353,3-Dimethylbutanal2×HCID 9810996Neotame

Product 2

HCID 134601AspartameHCID 9810996Neotame

Procedure

In a third embodiment of the present invention, neotame is synthesized by regenerating 3,3-dimethylbutyraldehyde from a hydrazone, semicarbazone or oxime of 3,3-dimethylbutyraldehyde by acidic hydrolysis or by oxidative cleavage in a solvent or a mixture of solvents and then adding aspartame under hydrogenation conditions with a catalyst to produce neotame.

Workup

  1. customby acidic hydrolysis
  2. additionby oxidative cleavage in a solvent or a mixture of solvents

Sources & evidence

ORD record
ord-65c9dc56481d45e6b7f57abe6c5d1939
Source dataset
uspto-grants-2007_10
Patent number
US07288670B2

Reaction notes

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