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

HRID 2217761Notes

Reaction equation

HRID 2217761 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 phosphateYield 80.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A sample of 505 mg (1.7 mmol) of 6-phosphocholinehexanoic acid in 11 ml of dimethylformamide was stirred at room temperature for 5 min. To this mixture, 1.3 g (5.5 mmol) of p-nitrophenyl trifluoroacetate was added. While stirring the resulting mixture, 0.43 ml (3.7 mmol) of 2,6-lutidine was added and the mixture was stirred until the 6-phosphocholinehexanoate completely dissolved. The reaction mixture was stirred at room temperature for an additional 6 hours. Afterwards, a 150 ml aliquot of ethyl ether was added to the reaction mixture to precipitate p-nitrophenyl 6-(O-phosphocholine)hydroxyhexanoate from solution. The supernatant was decanted and the oily product was dissolved in 5 ml of acetonitrile and precipitated again with ether. After the removal of solvent traces, 571 mg of p-nitrophenyl 6-(O-phosphocholine)hydroxyhexanoate was obtained at a yield of about 80%. The overall synthesis produced a yield of about 27%.

Workup

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

Sources & evidence

ORD record
ord-95fb0c46438444f187ec2e08f1c6a76c
Source dataset
uspto-grants-2008_08
Patent number
US07408075B1

Reaction notes

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