Hydrochloric Acid → HCID 69083988, Verbindung

A mixture of tert-butyl (3aR,5R,6S,7R,7aR)-5-(hydroxymethyl)-6,7-bis(4-methoxybenzyloxy)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl(methyl)carbamate (1 g, 1.74 mmol), KHCO3 (780 mg, 7.8 mmol), TBAB (28 mg, 0.09 mmol) and TEMPO (14 mg, 0.09 mmol) in dichloromethane (30 mL) and H2O (6 mL) was treated with NBS (620 mg, 3.5 mmol) overnight at room temperature. The reaction mixture was adjusted to acidic (pH at 3) with hydrochloric acid, and then extracted with dichloromethane (3×20 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum to provide a residue, which was purified by a silica gel column, eluted with 20˜50% ethyl acetate in petroleum ether to give compound 29 as a white solid (600 mg, 58%). (ES, m/z): [M+H]+ 589.0, 1H NMR (300 MHz, CDCl3) δ 7.25-7.32 (m, 2H), 6.85-6.90 (m, 2H), 6.08-6.10 (d, J=6.3 Hz, 1H), 4.50-4.62 (m, 5H), 4.22-4.29 (m, 2H), 3.97 (m, 1H), 3.81 (s, 6H), 3.34 (s, 3H), 1.54 (s, 9H).

1. extractionextracted with dichloromethane (3×20 mL)
2. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
3. concentrationconcentrated under vacuum
4. customto provide a residue, which
5. customwas purified by a silica gel column
6. washeluted with 20˜50% ethyl acetate in petroleum ether

ORD-Eintrag

ord-89187e5580c748e7afd4f1403f980465

Quelldatensatz

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08901087B2