Chlorotrimethylsilane → HCID 22870460, compound

Participants

Reaction Conditions

Reaction Steps

The acid hydrochloride (S,S)-2,7-Diamino-E-oct-4-ene-1,8-dioic acid dihydrochloride (1.59 g, 5.8 mmol) was suspended in hexamethyldisilazane (20 ml) and 1 ml of trimethylsilyl chloride was added. Then the suspension was refluxed overnight. The solvent was removed under reduced pressure and the residue was dissolved in anhydrous methylene chloride. This solution was cooled to 0° C. and a solution of 9-fluorenylmethyl chloroformate (3.10 g, 12 mmol) in methylene chloride was added. The solution was stirred for 1 hour before the cooling bath was removed. The next morning the solvent was evaporated and the residue was dissolved in THF. Then the mixture was quenched with 1N aqueous HCl and the solution was stirred for two hours. The organic solvent was removed and the water phase was extracted with chloroform. The organic layer was dried over magnesium sulfate and evaporated. The residue was dissolved in methylene chloride and precipitated with ether.

Provenance & Evidence