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Chloromethyl Chlorosulfate

Chloromethyl chlorosulfate is a promising electrophilic reagent capable of chloromethylation without generation of the potent carcinogen bischloromethyl ether as a by-product1

The chloromethyl ester shown below was prepared in greater than 90% yield by alkylation of the carboxylic acid using chloromethylchlorosulfate2.

Chloromethyl chlorosulfate reacts with N-Boc-protected L-Amino acids in a dichloromethane/water mixture under phase transfer conditions to yield chloromethyl esters3.

Chloromethyl phosphates are prepared in good yield using chloromethyl chlorosulfate and dialkyl phosphates under typical phase transfer conditions4.  The resulting compounds are useful intermediates in the synthesis of phosphonooxymethyl prodrugs which have been shown to be enzymatically labile.

  1. Org. Biomol. Chem., 2004, 2, 1554-1562
  2. Org. Biomol. Chem., 2006, 4, 2869-2873
  3. Bioorg. Med. Chem. Lett. 17, (2007) 465-470
  4. Tet. Lett., 43, (2002), 3793-3794