Acetic Anhydride → HCID 18603086, compound

HRID 1982152Notes

Reaction equation

HRID 1982152 reaction equation
[C:1]([O:18][CH2:19][C@H:20]([CH2:25][O:26]P(OCC[N+](C)(C)C)(O)=O)[O:21][C:22](=[O:24])[CH3:23])(=[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(OC(=O)C)(=O)C>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[C:1]([O:18][CH2:19][C@H:20]([CH2:25][OH:26])[O:21][C:22](=[O:24])[CH3:23])(=[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]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 5313207HCID 5313207, compound

Product 1

HCID 18603086HCID 18603086, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

An ester analog of PAF, 1-hexadecanoyl-2-acetyl-sn-glycero-3-phosphocholine, was made by acetylation of 1-hexadecanoyl-2-lyso-sn-glycero-3-phosphocholine in a reaction with 0.5 ml of acetic anhydride and 20 mg of 4-dimethylaminopyridine in 1.25 ml of toluene; the sealed tube was heated at 100° C. for 2 hours and, after evaporation of the solvents with a stream of N2, the products were extracted by the method of Bligh and Dyer as described in Canadian Journal of Biochemical Physiology, Vol. 3, pp. 911-917, 1959. The product, 1-hexadecanoyl-2-acetyl-sn-glycerol-3-phosphocholine, was then treated with phospholipase C to produce 1-hexadecanoyl-2-acetyl-sn-glycerol, which was estimated on the basis of TLC to have a purity >95%.

Workup

  1. customafter evaporation of the solvents with a stream of N2
  2. extractionthe products were extracted by the method of Bligh and Dyer
  3. additionThe product, 1-hexadecanoyl-2-acetyl-sn-glycerol-3-phosphocholine, was then treated with phospholipase C

Sources & evidence

ORD record
ord-c063f6568bef4a53b41d920b800119ca
Source dataset
uspto-grants-1986_06
Patent number
US04595681

Reaction notes

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