Methane → HCID 11789402, compound

Participants

Reaction Steps

A mixture of di-tert.-butyl 3-(N-ethoxycarbonyl-N-ethoxycarbonyloxyamino)trans-1-propenylphosphonate (8.60 g.) and 1 N hydrochloric acid (250 ml.) was refluxed for 15 hours. The resultant mixture was concentrated under reduced pressure to give a residue, which was dissolved in water (100 ml.) and treated with activated charcoal. The solution was concentrated under reduced pressure to give a residue (4 g.), which was dissolved in water (10 ml.) and adjusted to pH 4 with 1 N aqueous sodium hydroxide solution. The aqueous solution was passed through a column of anion exchange resin, Amberlite IRA-400 (trade name, made by Rhom & Hass Co.) (OH- form). The object compound was eluted from the resin with 1 N hydrochloric acid and then the eluate was concentrated under reduced pressure to give an oily residue (3.4 g.), which was dissolved in a mixture of water (0.5 ml.) and ethanol (20 ml.). The solution was adjusted to pH 4 with pyridine and concentrated under reduced pressure to give a residue, which was pulverized with methanol to give powder (1 g.). The powder was dissolved in water (0.5 ml.). To the aqueous solution was added methanol to give precipitates which were separated by filtration and dried to give powdery 3-(N-hydroxyamino)-trans-1-propenylphosphonic acid (280 mg.). Furthermore, the same object compound (120 mg.) was recovered from the mother liquor.

Provenance & Evidence