Acetonitrile → HCID 87416434, compound
Reaction equation
[NH2:1][CH:2]1[CH:17]([OH:18])[CH:6]2[O:7][CH:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:9][CH2:10][CH:5]2[CH2:4][CH:3]1[OH:19].[CH2:20]([S:22]N=C=O)C.[C:26](#[N:28])[CH3:27]>>[OH:19][C@H:3]1[C@H:2]([NH:1][C:20]([NH:28][CH2:26][CH3:27])=[S:22])[C@@H:17]([OH:18])[C@@H:6]2[O:7][C@H:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:9][CH2:10][C@H:5]2[CH2:4]1Participants
4
Conditions
- Temperature
- 60 °C
Procedure
To a suspension of the amine from above (85 mg, 0.32 mmol) in acetonitrile (3 mL) was added ethylthioisocyanate (34 mg, 0.39 mmol). The mixture was heated at 60° C. for 20 h. Solvent was evaporated to give the crude product. This was purified by silica gel chromatography, eluted with EtOAc to give pure rac-1-((2R,4aR,6R,7S,8R,8aR)-6,8-dihydroxy-2-phenylhexahydro-4H-benzo[d][1,3]dioxin-7-yl)-3-ethylthiourea (113 mg, 100%) as a white solid. 1H NMR (600 MHz, CD3OD) δ 7.52-7.50 (m, 2H), 7.40-7.31 (m, 3H), 5.60 (s, 1H), 4.15 (dd, J=10.8, 4.5, 1H), 3.69 (t, J=10.8, 1H), 3.65-3.51 (m, 5H), 1.81 (m, 2H), 1.23 (q, J=12.0, 1H), 1.20 (t, J=7.2, 1H). 13C NMR (151 MHz, CD3OD) 139.85, 129.81, 129.02, 129.03, 127.52, 102.90, 84.75, 75.14, 72.38, 71.88, 65.30, 35.21, 33.19, 14.64.