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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