L-Proline → HCID 178469806, compound

HRID 402672Notes

Reaction equation

HRID 402672 reaction equation
[O:1]=[C:2]1[CH2:6][O:5][C:4]([NH:7][C@@H:8]2[CH2:10][C@H:9]2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:3]1[C:17]([O:19][CH2:20][CH3:21])=[O:18].[NH:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][N:29]=2)[C:24]([CH:31]=O)=[CH:23]1.N1CCC[C@H]1C(O)=O>C(O)C>[NH:22]1[C:30]2=[N:29][CH:28]=[CH:27][CH:26]=[C:25]2[C:24]([CH:31]=[C:6]2[O:5][C:4]([NH:7][C@@H:8]3[CH2:10][C@H:9]3[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)=[C:3]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:2]2=[O:1])=[CH:23]1

Participants

5

Reactant 3

HCID 145742L-ProlineHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 70401985HCID 70401985, compound

Product 1

HCID 178469806HCID 178469806, compoundYield 14.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 4-oxo-2-{[(1R,2S)-2-phenylcyclopropyl]amino}-4,5-dihydrofuran-3-carboxylate (0.090 g, 0.31 mmol) which similarly prepared according to the procedure described in the Example 74, Fourth step and 7-azaindole-3-carboxaldehyde (0.045 g, 0.30 mmol) in ethanol (5.0 mL), L-proline (0.0035 g, 0.031 mmol) was added at ambient temperature. The mixture was refluxed for 2 days. Cooled to ambient temperature, the solvent was removed under reduced pressure then the residue was purified by preparative HPLC to afford the titled compound as solid (0.018 g, y. 14%).

Workup

  1. additionwas added at ambient temperature
  2. temperatureThe mixture was refluxed for 2 days
  3. customthe solvent was removed under reduced pressure
  4. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-4637b8cdfdc84135a719f003301fa3bd
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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