Maleic Anhydride → HCID 68768578, compound

HRID 2265193Notes

Reaction equation

HRID 2265193 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[C:8]1([C@H:14]([CH3:17])[CH2:15][NH2:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(O)(=O)C>[C:8]1([C@H:14]([CH3:17])[CH2:15][NH:16][C:1](/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5])=[O:7])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 1547950(2S)-2-Phenylpropan-1-amine

Product 1

HCID 68768578HCID 68768578, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of maleic anhydride (765 mg, 7.8 mmol) in acetic acid (20 mL) at rt was added (S)-2-phenylpropylamine. The mixture was stirred overnight then was partially concentrated. Water (50 mL) was added causing precipitation of the product acid. The white solid was collected by suction filtration, washed with water, and dried to provide 1.44 g (79%) of the pure acid. 1H NMR (400 MHz, CDCl3): 7.38-7.32 (m, 2H), 7.29-7.24 (m, 1H), 7.24-7.20 (m, 2H), 6.68 (br m, 1H), 6.29 (d J=12.7, 1H), 6.18 (d, J=12.7, 1H), 3.78-3.69 (m, 1H), 3.47-3.38 (m, 1H), 3.11-3.00 (m, 1H), 1.33 (d, J=7.0, 3H).

Workup

  1. concentrationthen was partially concentrated
  2. additionWater (50 mL) was added
  3. customprecipitation of the product acid
  4. filtrationThe white solid was collected by suction filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-ae454124356648dbb7884f5c21b10f73
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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