2,2,2-Trifluoroethanol → HCID 59806009, Verbindung

The compound 17 (400 mg, 1.52 mmol) and Et3N (850 ml, 6.10 mmol) were added to a stirring solution of triphosgene (181 mg, 0.61 mmol) in dichloromethane (8 mL) at −60° C. The reaction mixture was allowed to warm to room temperature and stirred for additional 2 h. 2,2,2-Trifluoroethanol (133 μl, 1.82 mmol) was added and the reaction mixture was stirred for 16 h, diluted with dichloromethane, washed with saturated aqueous NH4Cl, NaHCO3 and brine, dried over MgSO4, filtered and concentrated in vacuo. The solid residue was purified by flash chromatography (eluent 0.5-1% MeOH-dichloromethane) to afford the title compound 139 as a white solid (375 mg, 64% yield). 1H NMR: (DMSO) δ(ppm): 8.09 (d, J=6.8 Hz, 1H), 7.70 (d, J=8.8 Hz, 2H), 6.52 (d, J=8.8, 2H), 4.66 (q, J=9.1 Hz, 2H), 4.24-4.20 (m, 1H), 3.57-3.53 (m, 1H), 3.47-3.41 (m, 1H), 3.36-3.30 (m, 1H, overlap with water), 3.19-3.16 (m, 1H), 2.21-2.16 (m, 1H), 1.99-1.93 (m, 1H), 1.50 (s, 9H). LRMS (ESI): (calc.) 388.2; (obt.) 389.2 (M+H)+.

1. stirringthe reaction mixture was stirred for 16 h
2. washwashed with saturated aqueous NH4Cl, NaHCO3 and brine
3. dry with materialdried over MgSO4
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customThe solid residue was purified by flash chromatography (eluent 0.5-1% MeOH-dichloromethane)

ORD-Eintrag

ord-7eb138d06d6b4c5095bc1b1985e6b015

Quelldatensatz

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08030344B2