Triethylamine → HCID 86589077, compound

Participants

Reaction Steps

A solution of N-(2-Nitrobenzenesulfonamidoethyl)-cis-4-(benzoylthymin-1-yl)-D-proline diphenylmethyl ester (5) (1.20 g, 0.46 mmol) was dissolved in dichloromethane (5 mL). Boc2O (110 mg, 0.50 mmol) and triethylamine (5 mL) was added with stirring followed by 4-dimethylaminopyridine (10 mg, cat.). The yellow solution was stirred at room temperature for 6.5 h then evaporated to dryness to give N-2-(N′-4-Nitrobenzenesulfonyl-N′-tert-butoxycarbonyl)aminoethyl)-cis-4-(benzoylthymin-1-yl)-D-proline as yellow foam. Treatment of this material (max 0.46 mmol) with anhydrous K2CO3 (85 mg, 0.60 mmol) and thiophenol (66 mg, 0.60 mmol) in DMF (2 mL) at room temperature afforded an orange-yellow solution. The reaction mixture was then diluted with dichloromethane, washed with water and evaporated to dryness. The resulting yellow oil was purified by column chromatography (SiO2; EtOAc:Light Petroleum 1:1→2:1) to give the product as white foam 186.3 mg (62%, 2 steps); δH (200 MHz; CDCl3) 1.46 [9H, s, tBu CH3], 1.90 [3H, s, thymine CH3], 1.95 and 2.60 [2H, 2×m, CH2(3′)], 2.70-3.30 [6H, m, CH2(5′) and 2×aminoethyl CH2], 3.42 [1H, dd, CH(2′)], 5.12 [1H, m, CH(4′)], 5.28 [1H, br m, NH], 6.98 [1H, s, CHPh2], 7.36 [10H, m, Dpm aromatic CH], 7.50 [2H, t, Bz m-CH], 7.63 [1H, t, Bz p-CH], 7.90 [2H, d, Bz o-CH] and 7.98 [1H, s, thymine C(6)H]; m/z (APCI+) 676 (M+Na+, 18.5%), 653 (M+H+, 59), 597 (M−C4H8+, 25), 554 (M−Boc+, 9), 475 (26.5), 167 (Ph2CH+, 100); [α]D22+6.5 (c=1.06, CHCl3)

Provenance & Evidence