Oxygen → HCID 10159194, compound

Participants

Reaction Conditions

Reaction Steps

(S)-4-(4-Iodophenyl-1-sulfonyl)-2,2-dimethyl-thiomorpholine-3-carboxylic acid hydroxamide-O-Wang resin (15, Scheme 4) (5.0 g at 1 mmol/g loading, 5 mmol) was swelled in dioxane (40 mL). To this was added 4-hydroxymethylbenzene boronic acid (30 mL of a 0.5 M solution in dioxane/2.5 M aq. Na2CO3 [3 M equivalents relative to the boronic acid], 15 mmol). In a dry, oxygen free environment Pd(PPh3)4 (200 mg) was added, and the mixture was stirred while at 75° C. for 48 hours. Filtration and subsequent resin washing three times with alternating CH2Cl2 (20 mL) followed by THF (20 mL) gave the (S)-4-(4′-hydroxymethyl-biphenyl-4-sulfonyl)-2,2-dimethyl-thiomorpholine-3-carboxylic acid hydroxamide-O-Wang resin.

Provenance & Evidence