Lawesson's reagent → tert-Butyl (S)-5-thioxo-2-pyrrolidinecarboxylate
반응식
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]1참가 물질
4
실험 절차
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).
후처리
- temperatureat reflux for 15.5 h
- concentrationconcentrated
- customThe resultant residue was purified by flash chromatography (0 to 2 to 3 to 4% MeOH/CHCl3)
출처 및 근거
- ORD 기록
- ord-585925510a744f649fc62878129472d8
- 출처 데이터셋
- uspto-grants-2006_08
- 특허 번호
- US07094783B2
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