Methanol → Aspartame

HRID 845868Notes

Reaction equation

HRID 845868 reaction equation
[NH2:1][C@H:2]([C:7]([NH:9][C@H:10]([C:18]([OH:20])=[O:19])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:8])[CH2:3][C:4](=[O:6])[OH:5].[CH3:21]O>O.Cl>[CH3:21][O:19][C:18](=[O:20])[C@H:10]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[NH:9][C:7](=[O:8])[C@H:2]([CH2:3][C:4](=[O:5])[OH:6])[NH2:1]

Participants

5

Reactant 2

HCID 887MethanolHCID 93078L-Aspartyl-L-phenylalanine

Product 1

HCID 134601Aspartame

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

The α-L-aspartyl-L-phenylalanine (20 g, 0.071 mole) is dissolved in the mixture of water (12.2 ml) and methanol (9.5 ml) and concentrated hydrogen chloride (26 ml) is added while stirring for 48 hours at room temperature to obtain as a precipitate the hydrogen chloride salt of α-L-aspartyl-L-phenylalanine methyl ester (20.3 g, 0.055 mole). After filtration, the cake of precipitate is dissolved in 355 ml of water. Then, the mixture is adjusted to a pH of 4.8 with 50% caustic solution (3.8 ml) and kept overnight at 5° C. to obtain a precipitate and separated by filtration. The filtered precipitate is washed with water (13 ml) at 5° C. and dried to obtain α-L-aspartyl-L-phenylalanine methyl ester (12.4 g, 0.042 mole).

Workup

  1. additionis added

Sources & evidence

ORD record
ord-03b4ff70197a4bacb7a5b1513e9742ac
Source dataset
uspto-grants-1988_07
Patent number
US04760164

Reaction notes

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