Ethanol → HCID 86747278, compound

HRID 1655956Notes

Reaction equation

HRID 1655956 reaction equation
[NH2:1][C@@H:2]([CH2:6][CH2:7][N:8]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:18])[C:3]([OH:5])=[O:4].S(=O)(=O)(O)O.[CH2:24](O)[CH3:25]>>[NH2:1][C@@H:2]([CH2:6][CH2:7][N:8]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:18])[C:3]([O:5][CH2:24][CH3:25])=[O:4]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 22847937HCID 22847937, compound

Product 1

HCID 86747278HCID 86747278, compound

Procedure

A solution of 2-(S)-Amino-4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)butanoic acid (2 g) and concentrated sulphuric acid (0.5 mL) in absolute ethanol (30 mL) was heated under reflux for 15 h. The solvent was evaporated and the residue was treated with saturated sodium bicarbonate solution and extracted with ethyl acetate. The combined organic layers were dried (MgSO4) and evaporated. The residue was purified by chromatography using 20% ethyl acetate-dichloromethane then 75% ethyl acetate-dichloromethane as eluent to afford the title compound as a white solid (473 mg).

Workup

  1. temperatureunder reflux for 15 h
  2. customThe solvent was evaporated
  3. additionthe residue was treated with saturated sodium bicarbonate solution
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-8bf9e3ef21bc46d5a9a470c44aad72ff
Source dataset
uspto-grants-1993_10
Patent number
US05252560

Reaction notes

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