Triethylamine → N-(4-Hydroxy-3-oxo-2,3-dihydro-1H-inden-5-yl)-5-phenylpentanamide

HRID 340665Notes

Reaction equation

HRID 340665 reaction equation
Br.[NH2:2][C:3]1[C:11]([OH:12])=[C:10]2[C:6]([CH2:7][CH2:8][C:9]2=[O:13])=[CH:5][CH:4]=1.[C:14]1([CH2:20][CH2:21][CH2:22][CH2:23][C:24](O)=[O:25])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.P(C#N)(OCC)(OCC)=O.C(N(CC)CC)C>CN(C)C=O.C(OCC)C>[OH:12][C:11]1[C:3]([NH:2][C:24](=[O:25])[CH2:23][CH2:22][CH2:21][CH2:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:13])[CH2:8][CH2:7]2

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 16757Benzenepentanoic acidHCID 76257Diethyl cyanophosphonateHCID 673534616-Amino-7-hydroxy-2,3-dihydro-1H-inden-1-one hydrobromide

Product 1

HCID 57781279N-(4-Hydroxy-3-oxo-2,3-dihydro-1H-inden-5-yl)-5-phenylpentanamideYield 26.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

6-Amino-7-hydroxyindan-1-one hydrobromide (50 mg, 0.256 mmol) and 5-phenylvaleric acid (54.8 mg, 0.307 mmol) were dissolved in N,N-dimethylformamide (1.3 mL), diethyl cyanophosphate (45.7 μL, 0.307 mmol) and triethylamine (120 μL, 0.896 mmol) were added, and the mixture was stirred at room temperature for 15 min. The reaction solution was diluted with diethyl ether, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60) to give the title compound (21.8 mg, yield 26%).

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60)

Sources & evidence

ORD record
ord-1686fa72340c4af39303b86535ea67a8
Source dataset
uspto-grants-2014_11
Patent number
US08895591B2

Reaction notes

Loading…