Isopropanol → alpha-Formyl aspartic acid benzyl amide

HRID 2304842Notes

Reaction equation

HRID 2304842 reaction equation
[C:1]([CH2:4][CH:5]1[C:9](=[O:10])OC[N:6]1C=O)([OH:3])=[O:2].C(N(CC)CC)C.[CH2:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH:28]([OH:31])(C)C>>[CH2:20]([NH:27][C:28](=[O:31])[C@:5]([CH:9]=[O:10])([CH2:4][C:1]([OH:3])=[O:2])[NH2:6])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 4

HCID 3776IsopropanolHCID 7504BenzylamineHCID 8471TriethylamineHCID 153421764-Carboxymethyl-3-formyl-1,3-oxazolidin-5-one

Product 1

HCID 54330050alpha-Formyl aspartic acid benzyl amide

Procedure

The yellowish oil of example 1, dissolved in 100 ml isopropanol, is compounded with 14 ml (100 mmol) triethylamine and compounded with 10 ml (100 mmol) benzylamine. The mixture is heated for 3 h to 50° C. After removal of the isopropanol in a vacuum the residue is taken up in 100 ml 1 N HCl, agitated 1 h and then extracted several times with ethyl acetate. The saturated organic phases are dried over magnesium sulfate and after filtration the solvent is removed in a vacuum. 20 g (80 mmol) 80% of a slightly yellowish solid is obtained.

Workup

  1. temperatureThe mixture is heated for 3 h to 50° C
  2. customAfter removal of the isopropanol in a vacuum the residue
  3. extractionextracted several times with ethyl acetate
  4. dry with materialThe saturated organic phases are dried over magnesium sulfate
  5. filtrationafter filtration the solvent
  6. customis removed in a vacuum
  7. custom20 g (80 mmol) 80% of a slightly yellowish solid is obtained

Sources & evidence

ORD record
ord-b9992878cfb54b118538f1772f279549
Source dataset
uspto-grants-2002_08
Patent number
US06437145B1

Reaction notes

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