Sodium Iodide → 2-[(2-Benzyloxycarbonylaminoethyl)-tert-butoxycarbonylamino]-3-fluorobenzoic acid

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Reaction Steps

Sodium hydride (60%, 120 mg, 3.0 mmol) was added to a solution of 2-tert-butoxycarbonylamino-3-fluorobenzoic acid methyl ester from Example 20A (750 mg, 2.8 mmol) in DMF (8.0 ml) while cooling in an ice/water bath. The mixture was allowed to warm to room temperature and stirred for 30 min. (2-bromoethyl)carbamic acid benzyl ester (360 mg, 2.8 mmol) and sodium iodide (420 mg, 2.8 mmol) were added and the mixture was heated at 65° C. for 18 h. The mixture was cooled and evaporated in vacuo. The residue was partitioned between EtOAc and brine and the organic layer was dried and evaporated in vacuo. The residue was purified by flash chromatography on silica (EtOAc:pet. ether 30:70) to give a colourless gum; yield 340 mg, 27%.

Provenance & Evidence