Sulfuric Acid → HCID 86749654, compound
Reaction equation
[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C@H:6]([N:13]1[CH:17]=[C:16]([CH:18]=[O:19])[NH:15][C:14]1=[S:20])[CH2:7]2.[CH3:21][Mg]Cl.S(=O)(=O)(O)O>>[OH:19][CH:18]([C:16]1[NH:15][C:14](=[S:20])[N:13]([C@H:6]2[CH2:5][CH2:4][C:3]3[C:8](=[CH:9][C:10]([F:12])=[CH:11][C:2]=3[F:1])[CH2:7]2)[CH:17]=1)[CH3:21]Participants
Conditions
- Temperature
- 0 °C
Procedure
A mixture of (S)-3-(5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl)-2-thioxo-2,3-dihydro-1H-imidazole-5-carbaldehyde (178 mg, 0.6 mmol), prepared as in Example 22, and methylmagnesium chloride (3M, 0.4 mL, 1.2 mmol) was stirred at approximately 0° C. for 1 hour and at approximately 25° for an additional 1 hour. The mixture was treated with 5 mL of dilute sulfuric acid and extracted with ethyl acetate (2×). The combined extracts were dried (MgSO4) and concentrated and the residue was purified by flash chromatography on silica gel eluting with methylene chloride/methanol (98:2). The purified residue was further purified by preparative thin layer chromatography on silica gel eluting with methylene chloride/methanol (95:5) to give (S)-4-(1-hydroxy)ethyl-1-(5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl)-1,3-dihydroimidazole-2-thione (22 mg, 0.1 mmol), m.p. 210°-211° C.
Workup
- extractionextracted with ethyl acetate (2×)
- dry with materialThe combined extracts were dried (MgSO4)
- concentrationconcentrated
- customthe residue was purified by flash chromatography on silica gel eluting with methylene chloride/methanol (98:2)
- customThe purified residue was further purified by preparative thin layer chromatography on silica gel eluting with methylene chloride/methanol (95:5)
Sources & evidence
- ORD record
- ord-6e320b1e090742efb91171db6fcc98c8
- Source dataset
- uspto-grants-1998_02
- Patent number
- US05719280
Reaction notes
Loading…