Bromide ion → HCID 10229033, compound

HRID 1264969Notes

Reaction equation

HRID 1264969 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Mg].[Br-].C[O:16][C:17]([C@@H:19]1[CH2:24][CH2:23][CH2:22][CH2:21][N:20]1[S:25](=[O:40])(=[O:39])[NH:26][C:27]1[CH:32]=[C:31]([O:33][CH3:34])[C:30]([O:35][CH3:36])=[C:29]([O:37][CH3:38])[CH:28]=1)=O.[Cl-].[NH4+]>CCOCC.C1COCC1>[CH3:38][O:37][C:29]1[CH:28]=[C:27]([NH:26][S:25]([N:20]2[CH2:21][CH2:22][CH2:23][CH2:24][C@H:19]2[C:17](=[O:16])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:40])=[O:39])[CH:32]=[C:31]([O:33][CH3:34])[C:30]=1[O:35][CH3:36]

Participants

8

Reactant 5

HCID 259Bromide ionHCID 25517Ammonium ChlorideHCID 285561(5-Bromopentyl)benzeneHCID 5462224Magnesium2×HCID 10157093HCID 10157093, compound

Product 1

HCID 10229033HCID 10229033, compoundYield 1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

At 40° C., 5-phenylpentylbromide solution (1.15 g, 5 mmol) in ether (5 mL) was slowly added to magnesium turnings with vigorous agitation under Argon. The exothermic reaction was initialized after addition of one quarter of the bromide solution. Once the addition was completed, the suspension was heated at reflux for 30 minutes and most of magnesium was dissolved. The resulted 1M Grignard reagent was cooled to −70° C. and added the methyl ester (compound 90, 100 mg, 0.25 mmol) in THF solution (2 mL). The mixture was warmed to 25° C. and stirred at that temperature for 20 hours. Saturated amonium chloride (1 mL) was introduced to quench the reaction. The suspension was extracted with ether (1×50 mL). The organic phase was collected, dried and concentrated. The residue was purified by flash column chromatography (25% EtOAc in hexanes) followed by preparative TLC (1% THF in CH2Cl2) to give 1.2 mg (1% yield) of the title compound.

Workup

  1. customThe exothermic reaction
  2. additionOnce the addition
  3. temperaturethe suspension was heated
  4. dissolutionwas dissolved
  5. customto quench
  6. customthe reaction
  7. extractionThe suspension was extracted with ether (1×50 mL)
  8. customThe organic phase was collected
  9. customdried
  10. concentrationconcentrated
  11. customThe residue was purified by flash column chromatography (25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-9d0144f9deda4c48b3a4e525cd3e56ec
Source dataset
uspto-grants-2003_04
Patent number
US06544987B2

Reaction notes

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