Water ethanol → 2-Formylamino-3-hydroxy-4-ethyl-4-pentenoic acid ethyl ester

HRID 728861Notes

Reaction equation

HRID 728861 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH:10]([C:11]([CH2:13][CH3:14])=[CH2:12])[O:9][CH:8]=[N:7]1)=[O:5])[CH3:2].C([OH:17])C.O>>[CH2:1]([O:3][C:4](=[O:5])[CH:6]([NH:7][CH:8]=[O:17])[CH:10]([OH:9])[C:11]([CH2:13][CH3:14])=[CH2:12])[CH3:2]

Participants

3

Reactant 2

HCID 19096565Water ethanolHCID 542119745-(Buten-2-yl)-2-oxazoline-4-carboxylic acid ethyl ester

Product 1

HCID 216672992-Formylamino-3-hydroxy-4-ethyl-4-pentenoic acid ethyl ester

Procedure

The starting material is manufactured as follows: Reaction of 2-methylene-butyraldehyde with isocyanoacetic acid ethyl ester in a manneranalogous to that described in Example 1 yields 5-(buten-2-yl)-2-oxazoline-4-carboxylic acid ethyl ester. A solution of 16g of 5-(buten-2-yl)-2-oxazoline-4-carboxylic acid ethyl ester in 100 ml of ethanol/water (1:1) is heated at the boil, under reflux, for 15 hours. Thewhole is concentrated by evaporation in vacuo, the residue is taken up in 200 ml of dichloromethane, dried over sodium sulphate and filtered, and the filtrate is concentrated by evaporation to yield 2-formylamino-3-hydroxy-4-ethyl-4-pentenoic acid ethyl ester.

Workup

  1. temperatureunder reflux, for 15 hours
  2. concentrationThewhole is concentrated by evaporation in vacuo
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationthe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-c2157a93a0cb48af8d537b462539cfec
Source dataset
uspto-grants-1991_09
Patent number
US05051413

Reaction notes

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