Glutaric anhydride → (2R)-2-[(4-Carboxybutanoyl)oxy]-3-(hexadecanoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate

HRID 603324Notes

Reaction equation

HRID 603324 reaction equation
[C:1]([O:18][CH2:19][C@H:20]([CH2:22][O:23][P:24]([O:27][CH2:28][CH2:29][N+:30]([CH3:33])([CH3:32])[CH3:31])([OH:26])=[O:25])[OH:21])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[C:34]1(=[O:41])[O:40][C:38](=[O:39])[CH2:37][CH2:36][CH2:35]1.C(Cl)(Cl)Cl.CO>CN(C1C=CN=CC=1)C.ClCCl>[CH3:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([O:18][CH2:19][C@@H:20]([O:21][C:34]([CH2:35][CH2:36][CH2:37][C:38]([OH:40])=[O:39])=[O:41])[CH2:22][O:23][P:24]([O:27][CH2:28][CH2:29][N+:30]([CH3:32])([CH3:31])[CH3:33])([O-:26])=[O:25])=[O:17]

Participants

6

Reactant 3

HCID 7940Glutaric anhydrideHCID 460603HCID 460603, compoundHCID 21584188Chloroform methanol

Product 1

HCID 46907872(2R)-2-[(4-Carboxybutanoyl)oxy]-3-(hexadecanoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphateYield 42%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

PGPC (FIG. 1A, 1) was synthesized according to a modified version of the procedure by Watson et al. (J. Biol. Chem. 272, 13597-13607, 1997) and Subbanagounder et al. (Free Radic. Biol. Med. 28, 1751-1761, 2000). A solution of dry 1-palmitoyl-sn-glycero-3-phosphocholine (62 mg, 125 μmol), dry glutaric anhydride (70 mg, 613 μmol, 5 eq) and DMAP (p-(N,N′-dimethylamino)pyridine, 75 mg, 614 μmol, 5 eq) in 6 ml of anhydrous dichloromethane was magnetically stirred over night at 35° C. The reaction was monitored by TLC with CHCl3/MeOH/25% NH3 (65:35:5, v/v/v) as a developing system, and quenched by addition of 3 ml of MeOH. The resulting mixture was washed once with 1.8 ml of MeOH/H2O (1:1, v/v). After evaporation of the organic phase, excess DMAP was removed by trituration with 4 ml of diethylether. Removal of the supernatant afforded 32 mg of PGPC (42%, Rf=0.05).

Workup

  1. customPGPC (FIG. 1A, 1) was synthesized
  2. customquenched by addition of 3 ml of MeOH
  3. washThe resulting mixture was washed once with 1.8 ml of MeOH/H2O (1:1
  4. customAfter evaporation of the organic phase, excess DMAP
  5. customwas removed by trituration with 4 ml of diethylether
  6. customRemoval of the supernatant

Sources & evidence

ORD record
ord-782daf50ebaa4c8ea117eed99ced7f5e
Source dataset
uspto-grants-2011_03
Patent number
US07906674B2

Reaction notes

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