HCID 131724592, compound → HCID 178476994, compound

Participants

Reaction Steps

In case R2Y is R2O: Compounds of this type may be obtained by reaction shown in step f and g. These reaction may comprise (step f) reaction of compounds 4 with R2Br/NaH in DMSO at room temperature or benzyl-2,2,2-trichloroacetimidate/CF3SO3H in CH2Cl2/cyclohexane at room temperature (here the R2-side chains may be manipulated by reaction with 10% Pd/C/H2 in EtOH/dioxane) or the reaction is performed with PhOH/Ph3P/DIAD in THF at room temperature. All reactions may be followed by removal of the t-Bu-ether in TFA at 0° C. to room temperature. For the preparation of compounds of formula 7 (step g) compounds 6 (if m=0: for inversion of the configuration) may be obtained by thioacetate formation under Mitsunobu conditions (e.g. CH3COSH/Ph3P/DIAD in THF at 0° C. to room temperature) followed by formation of the thiol (e.g. by reaction with MeONa in MeOH at 0° C.; plus potential side chain manipulation with 1 N Na2CO3 in MeOH) or (if m=0: for retention of configuration) reaction of compounds 6 for e.g. formation of the mesylate (MeSO3H/Et3N/Ph3P/DIAD in toluene at 0° C. to 85° C. ) followed by preparation of the thioacetate (e.g. KSCOCH3 in DMF at 100° C.) and formation of the thiol (MeONa in MeOH at 0° C. ).

Provenance & Evidence