Indoline → Tert-butyl 3-[4-(2-{4-[(2,3-dihydro-indole-1-carbonyl)-amino]-3-methoxy-phenyl}-acetylamino)-phenyl]-butyrate

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Reaction Steps

Triphosgene (150 mg) was added to a stirred solution of tert-butyl 3-[4-({4-amino-3-methoxyphenyl}acetylamino)phenyl]butyrate (540 mg, Reference Example 2) in dichloromethane (50 ml) at 0-5° C. under an atmosphere of nitrogen. After stirring for one hour the mixture was treated with a solution of indoline (0.15 ml) in dichloromethane (2.5 ml) and triethylamine (0.51 ml). This mixture was allowed to stand at room temperature overnight and then evaporated. The residual gummy solid was suspended in water and the suspension was acidified to pH 1 by addition of hydrochloric acid. The resulting pale green solid was filtered and then subjected to flash chromatography on silica eluting with 0.2% to 1% methanol in dichloromethane to give the title compound (580 mg) as an off-white solid.

Provenance & Evidence