Lawesson's reagent → tert-Butyl (S)-5-thioxo-2-pyrrolidinecarboxylate
反応式
O=[C:2]1[NH:6][C@H:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4][CH2:3]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:23])=CC=1>C1C=CC=CC=1>[S:23]=[C:2]1[NH:6][C@H:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4][CH2:3]1参加物
4
実験手順
To a solution of t-butyl pyroglutamate (1a) (10.12 g, 54.6 mmol) in benzene (250 mL), was added Lawesson's reagent (11.05 g, 27.3 mmol). The mixture was stirred at reflux for 15.5 h, then concentrated. The resultant residue was purified by flash chromatography (0 to 2 to 3 to 4% MeOH/CHCl3) to afford 10.50 g (95%) of the title compound, 1b. 1H NMR (300 MHz, CDCl3) δ 7.27 (br s, 1H), 4.46–4.39 (m, 1H), 3.03–2.84 (m, 2H), 2.58–2.46 (m, 1H), 2.37–2.23 (m, 2H), 1.49 (s, 9H).
後処理
- temperatureat reflux for 15.5 h
- concentrationconcentrated
- customThe resultant residue was purified by flash chromatography (0 to 2 to 3 to 4% MeOH/CHCl3)
出典と根拠
- ORDレコード
- ord-585925510a744f649fc62878129472d8
- 出典データセット
- uspto-grants-2006_08
- 特許番号
- US07094783B2
反応ノート
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