1H-Indole-3-propanoic acid → HCID 21703095, compound

HRID 1954225Notes

Reaction equation

HRID 1954225 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](CCC(O)=O)=[CH:2]1.C(N1C=CN=C1)([N:17]1C=CN=C1)=O.[O:27]1C[CH2:30][CH2:29][CH2:28]1>>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH2:30][CH2:29][C:28]([NH2:17])=[O:27]

Participants

4

Reactant 3

HCID 37441H-Indole-3-propanoic acidHCID 8028TetrahydrofuranHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 21703095HCID 21703095, compound

Procedure

A solution of 3-indolepropionic acid (15 g, 79 mmol), 1,1'-carbonyldimidazole (16.7 g, 100 mmol) in anhydrous tetrahydrofuran (150 ml) was allowed to stir for 1.5 hours at room temperature. Then NH3 was bubbled through the solution for 2.5 hours at room temperature. The solvent was removed under vacuum, and the residue was dissolved in ethyl acetate (500 ml). The organic solution was washed with water (3×150 ml), dried over anhydrous sodium sulfate, filtered, and the solvent was removed under vacuum. The white solid was collected and dried under vacuum 10.42 g (96%); mp 124-125° C. MS EI m/e 188 (M+).

Workup

  1. customThen NH3 was bubbled through the solution for 2.5 hours at room temperature
  2. customThe solvent was removed under vacuum
  3. dissolutionthe residue was dissolved in ethyl acetate (500 ml)
  4. washThe organic solution was washed with water (3×150 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed under vacuum
  8. customThe white solid was collected
  9. customdried under vacuum 10.42 g (96%)

Sources & evidence

ORD record
ord-666f7e7df59046dcaa87d853320d803d
Source dataset
uspto-grants-2000_09
Patent number
US06121307

Reaction notes

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