1-Hexanethiol → N-(6-Methylthioquinolin-5-yl)-2-(hexylthio)-decanoic amide
Reaction equation
[CH3:1][S:2][C:3]1[C:4]([NH:13][C:14](=[O:25])[C@@H:15](Br)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:32]([SH:38])[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>C1COCC1>[CH3:1][S:2][C:3]1[C:4]([NH:13][C:14](=[O:25])[CH:15]([S:38][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2Participants
5
Procedure
(S)-N-(6-Methylthioquinolin-5-yl)-2-bromodecanoic amide (39 mg, 0.09 mmol) in 1 ml of dry THF was added slowly to a suspension containing cesium carbonate (67 mg, 0.20 mmol) and hexanethiol (13 mg, 0.11 mmol) in 2 ml of THF. After 18 hours, the reaction was quenched with 2 ml of 1N HCl and extracted with ethyl acetate (4×10 ml). The organic phase was purified by silica gel column chromatography (eluent: 100% CHCl3) to yield 25 mg (60% yield) of the desired product. 1H NMR (CDCl3) δ8.85 (1H, d, J=3 Hz), 8.62 (1H, s), 8.05 (1H, d, J=9 Hz), 8.00 (1H, d, J=9 Hz), 7.65 (1H, d, J=9 Hz), 7.40 (1H, dd, J=9, 9 Hz), 3.55 (1 H, t, J=8 Hz), 2.80 (2H, t, J=8 Hz), 2.50 (3H, s), 2.20-1.30 (22H, m), 0.91 (6H, t, J=Hz).
Workup
- customthe reaction was quenched with 2 ml of 1N HCl
- extractionextracted with ethyl acetate (4×10 ml)
- customThe organic phase was purified by silica gel column chromatography (eluent: 100% CHCl3)
Sources & evidence
- ORD record
- ord-2f9d9da7855f4145b3cf43c51a368936
- Source dataset
- uspto-grants-1996_03
- Patent number
- US05498786
Reaction notes
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