Indole-3-Acetic Acid → Ethyl cis-4-[(1H-indol-3-ylacetyl)amino]-5-oxo-1-phenyl-3-pyrrolidinecarboxylate

HRID 1590252Notes

Reaction equation

HRID 1590252 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([OH:13])=O)=[CH:2]1.[NH2:14][CH:15]1[C:19](=[O:20])[N:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:17][CH:16]1[C:27]([O:29][CH2:30][CH3:31])=[O:28]>CN(C=O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([NH:14][C@H:15]2[C:19](=[O:20])[N:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:17][C@H:16]2[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:13])=[CH:2]1

Participants

4

Reactant 2

HCID 802Indole-3-Acetic AcidHCID 19023548Ethyl 4-amino-5-oxo-1-phenyl-3-pyrrolidinecarboxylate

Product 1

HCID 67794878Ethyl cis-4-[(1H-indol-3-ylacetyl)amino]-5-oxo-1-phenyl-3-pyrrolidinecarboxylateYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of indole-3-acetic acid (248 mg, 1.42 mmol) in DMF (3 ml) was added 1,1-carbonyldiimidazole (230 mg, 1.42 mmol). After stirring for 2 h a solution of the aminopyrrolidinone of Example S (352 mg, 1.42 mmol) in DMF (1 ml) was added. After stirring for an additional 18 h the solvent was evaporated to give an oil which was chromatographed on silica gel eluting with EtOH/CH2Cl2 (2%-5%) to give 470 mg (91%) of the title compound as a solid. NMR (DMSO) 400 MHz : 3.25δ, m, 1H; 3.59δ, d, 2H; 3.88δ, t, 1H; 4.01δ, t, 1H; 4.65δ, q, 1H; 6.98δ, t, 1H; 7.08δ, t, 1H; 7.15δ, t, 1H; 7.24δ, d, 1H; 7.37, m, 3H; 7.56δ, d, 1H; 7.78δ, d, 2H; 8.62δ, d, 1H.

Workup

  1. additionwas added
  2. customwas evaporated
  3. customto give an oil which
  4. customwas chromatographed on silica gel eluting with EtOH/CH2Cl2 (2%-5%)

Sources & evidence

ORD record
ord-bce8d990aaf3447b9e96416730cb0188
Source dataset
uspto-grants-1993_04
Patent number
US05202344

Reaction notes

Loading…