Maleic Anhydride → (S)-1-[2-(Acetyloxy)-1-phenylethyl]-2,5-dihydro-1H-pyrrol-2,5-dione

HRID 53359Notes

Reaction equation

HRID 53359 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=O)[CH:3]=[CH:2]1.[C:8]1([C@@H:14]([CH2:16][OH:17])[NH2:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:18][CH2:19][O:20]C(C)=O.CC(O)=O>C1COCC1>[C:19]([O:17][CH2:16][C@@H:14]([N:15]1[C:1](=[O:7])[CH:2]=[CH:3][C:4]1=[O:6])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:20])[CH3:18]

Participants

5

Reactant 3

HCID 7923Maleic AnhydrideHCID 1347972-Amino-2-phenylethan-1-olHCID 22609514Ethyl acetate acetate

Product 1

HCID 9859949(S)-1-[2-(Acetyloxy)-1-phenylethyl]-2,5-dihydro-1H-pyrrol-2,5-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Maleic anhydride (358 mg, 3.65 mM) was added to (S)-(+)-2-phenylglycinol (500 mg, 3.65 mM) dissolved in 5 ml THF stirred under Ar. A precipitate formed immediately but redissolved after 1 hr. The mixture was stirred overnight. TLC (silica gel, EtOAc/HOAc 95:5) showed two spots, the product Rf 0.34, and a lower Rf spot, Rf 0.09. The THF was evaporated, and the residue was dissolved in 6 ml hot CH2Cl2. Crystals formed almost immediately in the hot mixture which was let stand at 5° for 2 hrs. The crystals were filtered, washed with cold CH2Cl2, and dried under vacuum to give the title compound: 600 mg (70%), mp. 131°-2°. ##STR48##

Workup

  1. customA precipitate formed immediately
  2. dissolutionredissolved after 1 hr
  3. stirringThe mixture was stirred overnight
  4. customThe THF was evaporated
  5. dissolutionthe residue was dissolved in 6 ml hot CH2Cl2
  6. customCrystals formed almost immediately in the hot mixture which
  7. customat 5°
  8. customfor 2 hrs
  9. filtrationThe crystals were filtered
  10. washwashed with cold CH2Cl2
  11. customdried under vacuum

Sources & evidence

ORD record
ord-f367abff887f4a088635e6a2d29fe2d5
Source dataset
uspto-grants-1997_04
Patent number
US05618946

Reaction notes

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