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 (3 M, 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 (2x). 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 (2x)
- 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-54c7b7eb57684212a5957ff0978cca50
- Source dataset
- uspto-grants-1996_07
- Patent number
- US05538988
Reaction notes
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