2-Amino-3-methylpentanoic acid → HCID 18696373, compound

HRID 1870470Notes

Reaction equation

HRID 1870470 reaction equation
[NH2:1][CH:2]([C:7]([OH:9])=[O:8])[CH:3]([CH2:5][CH3:6])[CH3:4].C(N(CC)CC)C.[CH:17]12[CH2:23][CH:20]([CH:21]=[CH:22]1)[CH:19]1[C:24]([O:26][C:27](=O)[CH:18]21)=[O:25]>C1(C)C=CC=CC=1>[C:7]([CH:2]([N:1]1[C:24](=[O:25])[CH:19]2[CH:18]([CH:17]3[CH2:23][CH:20]2[CH:21]=[CH:22]3)[C:27]1=[O:26])[CH:3]([CH3:4])[CH2:5][CH3:6])([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 7912-Amino-3-methylpentanoic acidHCID 8471TriethylamineHCID 13223826-62-0

Product 1

HCID 18696373HCID 18696373, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of (dl)-isoleucine (2.03 g, 15.5 mmol) in toluene (40 mL) was added triethylamine (2.4 mL, 17.2 mmol). The mixture was heated to reflux temperature and bicyclo[2.2.1]hept-5-en-2,3-dicarboxylic anhydride (2.53 g, 15.5 mmol) was added. The reaction mixture was kept at reflux temperature and allowed to react for 4 hrs. After cooling to room temperature, the solvent was evaporated and the residue dissolved in H2O. The aqueous solution was washed with EtOAc, acidified with conc. HCl until pH=1, and extracted with EtOAc. The organic phase was washed with 5% HCl and brine and dried over Na2SO4. Removal of the solvent gave a white solid (3.72 g) which was recrystallized from EtOAc/hexane to yield the pure product as colorless crystals: mp=109° C.

Workup

  1. temperatureThe mixture was heated
  2. additionwas added
  3. temperatureat reflux temperature
  4. customto react for 4 hrs
  5. customthe solvent was evaporated
  6. dissolutionthe residue dissolved in H2O
  7. washThe aqueous solution was washed with EtOAc
  8. extractionextracted with EtOAc
  9. washThe organic phase was washed with 5% HCl and brine
  10. dry with materialdried over Na2SO4
  11. customRemoval of the solvent

Sources & evidence

ORD record
ord-c757034e37154ddfa66e6d07d78d5484
Source dataset
uspto-grants-2000_08
Patent number
US06096811

Reaction notes

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