L-Phenylalanine → HCID 10977466, compound

HRID 487337Notes

Reaction equation

HRID 487337 reaction equation
N[C@H:2]([C:10]([OH:12])=O)CC1C=CC=CC=1.[O:13]=[C:14]1[CH:19]([CH2:20][C:21]([NH2:23])=O)[NH:18][C:17](=[O:24])[CH2:16][NH:15]1.[C:25](OC(=O)C)(=[O:27])[CH3:26]>>[C:25]([N:18]1[CH:19]([CH2:20][C:21]#[N:23])[C:14](=[O:13])[N:15]([C:10](=[O:12])[CH3:2])[CH2:16][C:17]1=[O:24])(=[O:27])[CH3:26]

Participants

4

Reactant 3

HCID 6140L-PhenylalanineHCID 7918Acetic AnhydrideHCID 10888355HCID 10888355, compound

Product 1

HCID 10977466HCID 10977466, compound

Procedure

A method of preparing α-APM derivatives without using an expensive L-phenylalanine is provided, wherein 2,5-dioxopiperazine-3-acetamide is reacted with acetic anhydride to give N,N'-diacetyl-6-cyanomethyl-2,5-dioxopiperazine, which is then reacted with benzaldehyde in the presence of a strong base to give 1-acetyl-3-benzylidene-6-cyanomethyl-2,5-dioxopiperazine. This is treated with hydrazine to give 3-benzylidene-6-cyanomethyl-2,5-dioxopiperazine, which is then reduced to prepare 3-benzyl-6-cyanomethyl-2,5-dioxopiperazine, which is converted by reaction with methanol in the presence of a strong acid to an α-APM derivative for use as a sweetener.

Workup

  1. customA method of preparing α-APM derivatives
  2. customis provided

Sources & evidence

ORD record
ord-3e32e99d8c4f40ada791a3c6a0d9d410
Source dataset
uspto-grants-1994_03
Patent number
US05294714

Reaction notes

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