methyl 2-iodoacetate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6-t-Butoxycarbonylamino-perhydro-1,4-thiazepin-5-one (0.1 g) and methyl iodoacetate (0.1 g) are dissolved in 1 ml of THF. Sodium hydride (50% suspension in oil) is added in batches. After one hour at room temperature, the reaction is quenched with 2 ml of 10% ammonium chloride solution. The crude product is extracted into methylene chloride, and subsequently chromatographed on silica gel (40:1 chloroform-methanol) to yield the pure product (0.09 g). The NMR spectrum is consistent with the assigned structure. A sample is obtained by recrystallization from ether-methanol and analyzes for C13H22N2O5S. the reaction is quenched with 2 ml of 10% ammonium chloride solution The crude product is extracted into methylene chloride subsequently chromatographed on silica gel (40:1 chloroform-methanol)