(4-Carboxybutyl)triphenylphosphonium bromide → HCID 54557606, compound

HRID 374824Notes

Reaction equation

HRID 374824 reaction equation
[Br-].[C:2]([CH2:5][CH2:6][CH2:7][CH2:8][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:4])=[O:3].CC(C)([O-])C.[K+].C(NC1C=CC(C2C([C:50]([C:52]3[C:53]([C:58]4[CH:63]=[CH:62][C:61]([NH:64][C:65](=[O:67])[CH3:66])=[CH:60][CH:59]=4)=[N:54][CH:55]=[CH:56][CH:57]=3)=O)=CC=CN=2)=CC=1)(=O)C>O1CCCC1>[C:65]([NH:64][C:61]1[CH:60]=[CH:59][C:58]([C:53]([C:52]2[CH:50]=[N:54][CH:55]=[CH:56][CH:57]=2)=[CH:8][CH2:7][CH2:6][CH2:5][C:2]([OH:4])=[O:3])=[CH:63][CH:62]=1)(=[O:67])[CH3:66]

Participants

5

Reactant 3

HCID 161236(4-Carboxybutyl)triphenylphosphonium bromideHCID 23665647Potassium tert-butoxideHCID 67745971HCID 67745971, compound

Product 1

HCID 54557606HCID 54557606, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 307 g of 4-carboxybutyltriphenylphosphonium bromide and 233 g of potassium tert.butoxide in 2.8 liters of tetrahydrofuran are added, at -40° C., 140 g of 4-acetylaminophenyl-3-pyridyl-ketone and this mixture is stirred for 2 hours. The reaction mixture is decomposed by the addition of ice water and evaporated down. The residue is taken up in water and washed with ethyl acetate. The aqueous phase is acidified to pH 5 to 6 and extracted with ethyl acetate. The organic phase is concentrated by evaporation and the residue is recrystallised from ethyl acetate/diisopropylether.

Workup

  1. additionare added, at -40° C.
  2. customevaporated down
  3. washwashed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. concentrationThe organic phase is concentrated by evaporation
  6. customthe residue is recrystallised from ethyl acetate/diisopropylether

Sources & evidence

ORD record
ord-b540687b52e4443e827dd1fa1c729479
Source dataset
uspto-grants-1996_01
Patent number
US05482948

Reaction notes

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