Triethylamine → HCID 86592245, compound

HRID 456664Notes

Reaction equation

HRID 456664 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](Cl)=[O:7].[C:9]1([C@@H:15]([NH2:17])[CH3:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C>C(Cl)Cl>[C:9]1([C@@H:15]([NH:17][C:6]([C:2]2[NH:1][CH:5]=[CH:4][CH:3]=2)=[O:7])[CH3:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 758181-Phenethylamine, (-)-HCID 224558Pyrrole-2-carbonyl chloride

Product 1

HCID 86592245HCID 86592245, compoundYield 40.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1H-pyrrole-2-carbonyl chloride (1.3 g, 10 mmol) (from Example 30) in DCM (20 mL) was added (S)-1-phenyl-ethylamine (1.4 g, 11.55 mmol) (Aldrich, Milwaukee, Wis.), followed by triethylamine (1.5 mL). The reaction was stirred at room temperature for overnight. The reaction was washed with 1N NaOH, water, brine, dried and concentrated to give 867 mg (40%) of 1H-pyrrole-2-carboxylic acid ((S)-1-phenyl-ethyl)-amide.

Workup

  1. washThe reaction was washed with 1N NaOH, water, brine
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-72e56712e4f7418988cbd580125c1fd9
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

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