Potassium Iodide → HCID 69842851, compound

HRID 1860281Notes

Reaction equation

HRID 1860281 reaction equation
[ClH:1].[NH2:2][N:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH2:15][C:14]3([CH2:20][CH2:19][N:18]([CH2:21]C(OCC)=O)[CH2:17][CH2:16]3)[O:13][N:12]=2)=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].BrC[CH2:35][CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39].[I-].[K+]>C(O)C.O>[ClH:1].[NH2:2][N:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH2:15][C:14]3([CH2:16][CH2:17][N:18]([CH2:21][CH2:35][CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:19][CH2:20]3)[O:13][N:12]=2)=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 84580Ethyl 5-bromovalerate2×HCID 86584287HCID 86584287, compound

Product 1

HCID 69842851HCID 69842851, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 1.1 g (4.56 mmol) of the intermediate from Example 5. Step B in 20 ml dry ethanol were added 1.26 g (9.12 mmol) potassium carbonate. After 15 min stirring at room temperature 1.03 g (4.93 mmol) ethyl 5-bromopentanoate and a catalytic amount of potassium iodide were added. It was stirred over night at room temperature, and the reaction was brought to completion by addition of another 0.52 g (2.49 mmol) ethyl 5-bromopentanoate and heating with reflux for 3 h. The mixture was poured into water and extracted three times with ethyl acetate. The combined organic layers were washed with water, dried over sodium sulfate, and concentrated under reduced pressure. The title compound was obtained by chromatography on silica gel with dichloromethane/ethanol 95:5 followed by 92:8.

Workup

  1. temperatureheating
  2. temperaturewith reflux for 3 h
  3. extractionextracted three times with ethyl acetate
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c11d51a96a124acd8b65b9ead9a172b7
Source dataset
uspto-grants-2003_03
Patent number
US06528534B2

Reaction notes

Loading…