Water → HCID 12621985, compound

HRID 1277623Notes

Reaction equation

HRID 1277623 reaction equation
[C:1]([NH:7][C@H:8]([C:10]([OH:12])=O)[CH3:9])(=[O:6])[CH2:2][CH:3]([CH3:5])[CH3:4].N1C=CC=CC=1.[OH2:19].[O:20]1[CH2:24]C[CH2:22][CH2:21]1>>[CH2:21]([O:20][C:24](=[O:19])[C:10](=[O:12])[CH:8]([NH:7][C:1](=[O:6])[CH2:2][CH:3]([CH3:4])[CH3:5])[CH3:9])[CH3:22]

Participants

5

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 8028TetrahydrofuranHCID 129285N-(3-Methyl-1-oxobutyl)-L-alanine

Product 1

HCID 12621985HCID 12621985, compound

Procedure

Ethyl oxalyl chloride (212 g) was added dropwise with stirring to a solution of isovalerylalanine (136 g) and pyridine (186.5 g) in anhydrous tetrahydrofuran (500 ml) at a rate sufficient to initiate refluxing. The reaction mixture was stirred and heated at reflux for 5 hours. The cooled reaction mixture was treated with water (1000 ml) and extracted with ethyl acetate (4×400 ml). The combined organic extracts were washed with water (3×200 ml) and dried (anhydrous sodium sulphate). Removal of solvent provided a yellow syrup which was evaporated with benzene (2×200 ml) to yield the isomeric enol esters of the title compound.

Workup

  1. temperatureto initiate refluxing
  2. temperatureheated
  3. temperatureat reflux for 5 hours
  4. customThe cooled reaction mixture
  5. extractionextracted with ethyl acetate (4×400 ml)
  6. washThe combined organic extracts were washed with water (3×200 ml)
  7. dry with materialdried (anhydrous sodium sulphate)
  8. customRemoval of solvent
  9. customprovided a yellow syrup which
  10. customwas evaporated with benzene (2×200 ml)

Sources & evidence

ORD record
ord-ba6fccb4be5c4dd6ab1789ed47479996
Source dataset
uspto-grants-1981_07
Patent number
US04278673

Reaction notes

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