Water → HCID 14631422, compound

HRID 728840Notes

Reaction equation

HRID 728840 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH:10]([CH:11]=[CH2:12])[O:9][CH:8]=[N:7]1)=[O:5])[CH3:2].[OH2:13].C(N(CC)CC)C>O1CCCC1.ClCCl>[CH2:1]([O:3][C:4](=[O:5])[CH:6]([NH:7][CH:8]=[O:13])[CH:10]([OH:9])[CH:11]=[CH2:12])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 14631421HCID 14631421, compound

Product 1

HCID 14631422HCID 14631422, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

128 g of the 5-vinyl-2-oxazoline-4-carboxylic acid ethyl ester are dissolved in 70 ml of tetrahydrofuran, and 27.4 g of water and 3.5 g of triethylamine are added. The reaction mixture is stirred for 62 hours at 65°-70° and, having been cooled, is taken up in 200 ml of dichloromethane. The solution is dried over 200 g of magnesium sulphate, filtered and concentrated by evaporation in vacuo. Purification by column chromatography (silica gel;hexane/ethyl acetate 3:2) of the viscous oil that remains yields 2-formylamino-3-hydroxy-4-pentenoic acid ethyl ester in the form of a diastereoisomeric mixture, m.p. 50°-51°.

Workup

  1. temperaturehaving been cooled
  2. dry with materialThe solution is dried over 200 g of magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated by evaporation in vacuo
  5. customPurification by column chromatography (silica gel;hexane/ethyl acetate 3:2) of the viscous oil that

Sources & evidence

ORD record
ord-c89effe707e7450ca4a063a12b7c5aee
Source dataset
uspto-grants-1991_09
Patent number
US05051413

Reaction notes

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