Citraconic Anhydrides → HCID 86748897, compound

HRID 1756873Notes

Reaction equation

HRID 1756873 reaction equation
[CH3:1][NH:2][C:3](=[O:15])[C@H:4]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)[NH2:5].[C:16]1(=[O:23])[O:22][C:20](=[O:21])[CH:19]=[C:17]1[CH3:18]>C(Cl)(Cl)Cl>[C:16]([C:17]([CH3:18])=[CH:19][C:20]([NH:5][C@H:4]([C:3]([NH:2][CH3:1])=[O:15])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=1)=[O:21])([OH:23])=[O:22]

Participants

4

Reactant 2

HCID 12012Citraconic AnhydridesHCID 14303038O-methyl-L-tyrosine N-Methylamide

Product 1

HCID 86748897HCID 86748897, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixed solution consisting of 50 g of N,O-dimethyltyrosine amide, 400 ml of dry chloroform and 27 g of citraconic anhydride was stirred at room temperature for 6 hours, concentrated under a reduced pressure, subjected to a silica gel column chromatography and eluted with chloroform-methanol-acetic acid to obtain 20 g of Nα -(3-carboxy-2-butenoyl)-N,O-dimethyltyrosine amide.

Workup

  1. concentrationconcentrated under a reduced pressure
  2. washeluted with chloroform-methanol-acetic acid

Sources & evidence

ORD record
ord-e29755f125b3461f9d011e27cae79225
Source dataset
uspto-grants-1995_08
Patent number
US05442110

Reaction notes

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