4-Nitrobenzenesulfonyl chloride → HCID 131733459, compound

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Reaction Steps

A solution of N-({5-[(1R)-1-amino-2-{[tert-butyl(dimethyl)silyl]oxy}ethyl]-thiophen-2-yl}methyl)-Nα-(methoxycarbonyl)-β-phenyl-L-phenylalaninamide (125 mg, 0.220 mmol) in dichloromethane (4.4 mL) was treated with diisopropylethylamine (0.046 mL, 0.264 mmol) and solid p-nitrobenzensulfonyl chloride (59 mg, 0.264 mmol) and the mixture was stirred at room temperature for 18 hours, quenched with saturated NaHCO3 (0.5 mL), diluted with DCM, washed with sat. NaHCO3, dried over MgSO4, filtered and concentrated. The crude was purified on silica gel 10%-50% ethyl acetate in hexane to provide the title compound. 1H NMR (CD3)2CO) δ 8.39 (2H), 8.05 (2H), 7.67 (1H), 7.41 (5H), 7.30-7.15 (6H), 6.65 (1H), 6.42 (1H), 6.30 (1H), 5.10 (1H), 4.72 (1H), 4.50 (1H), 4.23 (1H), 4.13 (1H), 3.82 (2H), 3.49 (3H), 0.84 (9H), 0.01 (6H).

Provenance & Evidence