Acyloxymethyl as a drug protecting group. Synthesis and reactivity of N-(acyloxymethyl)sulfonamide prodrugs was written by Calheiros, Teresa;Iley, Jim;Lopes, Francisca;Moreira, Rui. And the article was included in Bioorganic & Medicinal Chemistry Letters in 1995.Application In Synthesis of Chloromethyl benzoate This article mentions the following:
Tertiary N-(acyloxymethyl)sulfonamide prodrugs R1SO2NR2CH2OCOR3 (R1 = 4-MeC6H4, 4-ClC6H4, 4-O2NC6H4, 4-H2NC6H4, R2 = Me, Et, Pr CHMe2, Bu, Q, Q1, R3 = Ph, CMe3, Q2), encompassing penicillin and sulfonamide antibiotics, have been synthesized. The pH-independent hydrolysis of these compounds occurs via the rate-determining formation of an N-sulfonyl iminium ion. SCF-MO calculations using the PM3 method indicate that iminium ion formation is slightly favored, when compared with the corresponding amides, by ca. 10 kJmol-1. In the experiment, the researchers used many compounds, for example, Chloromethyl benzoate (cas: 5335-05-7Application In Synthesis of Chloromethyl benzoate).
Chloromethyl benzoate (cas: 5335-05-7) belongs to organic chlorides. Chlorinated organic compounds are found in nearly every class of biomolecules and natural products including alkaloids, terpenes, amino acids, flavonoids, steroids, and fatty acids.While alkyl bromides and iodides are more reactive, alkyl chlorides tend to be less expensive and more readily available. Alkyl chlorides readily undergo attack by nucleophiles.Application In Synthesis of Chloromethyl benzoate
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics