Pyridine → Ethyl phosphonoacetate

To a solution of 1-O-octadecyl-2,2-dimethoxy-1,3-propanediol (1.92 gm, 5 mmol) and ethyl phosphonoformate (1.19 g, 5 mmol) in dry pyridine (50 mL), cooled in an ice-salt bath, was added a solution of N,N-dicyclohexylcarbodiimide (3.1 g, 15 mmol) in dry dichloromethane (20 mL). The resulting mixture was stirred at room temperature over. The mixture was filtered, and the filtrate was concentrated to dryness. The residue was flash chromatographed with a gradient of 0-10% methanol in dichloromethane to give the target compound. In a similar manner, use of ethyl phosphono-acetate resulted in the corresponding 1-O-octadecyl-2,2-dimethoxy-1,3-propane diol-3-ethylphosphonoacetate.

1. filtrationThe mixture was filtered
2. concentrationthe filtrate was concentrated to dryness
3. customchromatographed with a gradient of 0-10% methanol in dichloromethane
4. customto give the target compound

ORD record

ord-5d381bcf66334737a0f30d3a1b5cc307

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07517858B1