Allyl bromide → 3-(Allyl-benzyloxycarbonyl-amino)-5-oxazol-2-yl-benzoic acid methyl ester

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Reaction Steps

3-Benzyloxycarbonylamino-5-oxazol-2-yl-benzoic acid methyl ester (330 mg, 0.927 mmol, I eq) is dissolved in THF (10 ml). NaH (48 mg, 60%,1.21 mmol, 1.3 eq) is added in portions, and the reaction mixture is stirred for 30 min at rt. TBAI (35 mg, 92.7 μmol, 0.1 eq) and allyl bromide (119 μl, 1.39 mmol, 1.5 eq) are added, and the reaction mixture is stirred for 20 h and then quenched with HCl (1N in H2O). The aqueous phase is extracted with EtOAc. The organic layer is washed with brine, dried over sodium sulfate, filtered and concentrated to give the product.

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