Potassium Iodide → HCID 69597625, compound

HRID 1796795Notes

Reaction equation

HRID 1796795 reaction equation
[C:1]([O:5][C:6](=[O:26])[CH2:7][NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:14][CH:13]=1)(=[O:11])=[O:10])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH:34]([CH3:38])[CH2:35][CH:36]=[CH2:37].[I-].[K+]>O.CN(C)C=O>[C:1]([O:5][C:6](=[O:26])[CH2:7][N:8]([S:9]([C:12]1[CH:13]=[CH:14][C:15]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:16][CH:17]=1)(=[O:11])=[O:10])[CH2:37][CH2:36][CH2:35][CH:34]=[CH2:38])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonate2×HCID 1416754-Bromopent-1-ene2×HCID 69597605HCID 69597605, compound2×

Product 1

HCID 69597625HCID 69597625, compoundYield 83.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

To a mixture of [4-Benzyloxybenzenesulfonylamino]-acetic acid tert-butyl ester (compound of formula XV, 91 g, 240 mmol), cesium carbonate (86 g, 264 mmol) and dimethylformamide (240 ml) was added 4-bromopentene (39 g, 264 mmol) and potassium iodide (39 g). After stirring at about 23° C. for about 24 hours, the mixture was heated to about 55° C. After stirring for about 4 hours, the mixture was treated with additional 4-bromopentene (3.94 g, 26.4 mmol) and cesium carbonate (8.61 g, 26.4 mmol) and was stirred at about 65° C. for about 12 hours. The mixture was cooled to about 23° C., diluted with water and was extracted with ethyl acetate. The organic phase was washed 3 times with water, dried over sodium sulfate, filtered and concentrated in vacuo to afford 89 g of [(4-benzyloxy-benzenesulfonyl)-pent-4-enyl-amino]-acetic acid tert-butyl ester (compound of formula XVI) as a colorless syrup.

Workup

  1. temperaturethe mixture was heated to about 55° C
  2. stirringAfter stirring for about 4 hours
  3. stirringwas stirred at about 65° C. for about 12 hours
  4. temperatureThe mixture was cooled to about 23° C.
  5. extractionwas extracted with ethyl acetate
  6. washThe organic phase was washed 3 times with water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4fa216e28468494da45cf9baec01bf21
Source dataset
uspto-grants-2006_04
Patent number
US07030242B2

Reaction notes

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