Diethyl Ether → 6-(4-Nitrophenoxy)-6-oxohexyl 2-(trimethylazaniumyl)ethyl phosphate

HRID 2217760Notes

Reaction equation

HRID 2217760 reaction equation
[CH3:1][N+:2]([CH2:5][CH2:6][O:7][P:8]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])([OH:10])=[O:9])([CH3:4])[CH3:3].FC(F)(F)C(O[C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=1)=O.N1C(C)=CC=CC=1C.C(OCC)C>CN(C)C=O>[CH3:1][N+:2]([CH2:5][CH2:6][O:7][P:8]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=1)=[O:18])([O-:10])=[O:9])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 79372,6-LutidineHCID 695694-Nitrophenyl trifluoroacetateHCID 29986451HCID 29986451, compound

Product 1

HCID 1264286-(4-Nitrophenoxy)-6-oxohexyl 2-(trimethylazaniumyl)ethyl phosphate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A sample of 6-phosphocholinehexanoic acid in dimethylformamide is stirred at room temperature for 5 min. To this mixture, approximately a three fold molar excess of p-nitrophenyl trifluoroacetate is added. While stirring the resulting mixture, approximately a 2 fold molar excess of 2,6-lutidine is added and the mixture is stirred until the 6-phosphocholinehexanoate completely dissolves. The reaction mixture is stirred at room temperature for an additional 6 hours. Afterwards, an aliquot of ethyl ether is added to the reaction mixture to precipitate p-nitrophenyl 6-(O-phosphocholine)hydroxyhexanoate from solution. The supernatant is decanted and the oily product is dissolved in acetonitrile and is precipitated again with ether. After the removal of solvent traces, p-nitrophenyl 6-(O-phosphocholine)hydroxyhexanoate is obtained.

Workup

  1. stirringthe mixture is stirred until the 6-phosphocholinehexanoate
  2. dissolutioncompletely dissolves
  3. stirringThe reaction mixture is stirred at room temperature for an additional 6 hours
  4. customto precipitate p-nitrophenyl 6-(O-phosphocholine)hydroxyhexanoate from solution
  5. customThe supernatant is decanted
  6. dissolutionthe oily product is dissolved in acetonitrile
  7. customis precipitated again with ether
  8. customAfter the removal of solvent traces

Sources & evidence

ORD record
ord-ce63328153c741f9ac93f73bfda0a0c5
Source dataset
uspto-grants-2008_08
Patent number
US07408075B1

Reaction notes

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