Benzenepentanoic acid → HCID 20768294, compound

HRID 985152Notes

Reaction equation

HRID 985152 reaction equation
[NH2:1][CH2:2][C:3]1[N:4]([CH3:22])[C:5](=[O:21])[C:6]2[C:11]([C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:10][C:9]([O:19][CH3:20])=[CH:8][CH:7]=2.[C:23]1([CH2:29][CH2:30][CH2:31][CH2:32][C:33](O)=[O:34])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.Cl.CN(C)CCCN=C=NCC.ON1C2N=CC=CC=2N=N1.C(=O)(O)[O-].[Na+]>CN(C)C=O.O>[CH3:20][O:19][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[C:5](=[O:21])[N:4]([CH3:22])[C:3]([CH2:2][NH:1][C:33](=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[C:12]2[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

8

Reactant 5

HCID 16757Benzenepentanoic acidHCID 181649HOAtHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22555938HCID 22555938, compound

Product 1

HCID 20768294HCID 20768294, compoundYield 82,352.898%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 41 (50 mg, 0.170 mmol), 5-phenylvaleric acid (33 mg, 0.187 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (36 mg, 0.187 mmol), 1-hydroxy-7-azabenzotriazole (25 mg, 0.187 mmol) in N,N-dimethylformamide was stirred at room temperature for 18 h. The contents of the reaction flask were poured into water and sat. sodium bicarbonate. Extracted with methylene chloride (3×). The combined organic extracts were washed with 5% potassium bisulfate, dried with sodium sulfate (anh.) and filtered. Concentration of the filtrate in vacuo followed by trituration with ether gave 42 as a white solid (62 mg, 140 mmol, 82.1%).

Workup

  1. extractionExtracted with methylene chloride (3×)
  2. washThe combined organic extracts were washed with 5% potassium bisulfate
  3. dry with materialdried with sodium sulfate (anh.)
  4. filtrationfiltered

Sources & evidence

ORD record
ord-71fb13667a5a45b4873ee86a2f52d62a
Source dataset
uspto-grants-2005_03
Patent number
US06870055B2

Reaction notes

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