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

HRID 1682293Notes

Reaction equation

HRID 1682293 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 manner analogous to that described in Example 1 yields 5-(buten-2-yl)-2-oxazoline-4-carboxylic acid ethyl ester. A solution of 16 g 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. The whole 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. concentrationThe whole 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-9baf809920d64bed948e00cf5994861f
Source dataset
uspto-grants-1992_12
Patent number
US05175344

Reaction notes

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