Lawesson's reagent → tert-Butyl (S)-5-thioxo-2-pyrrolidinecarboxylate

HRID 10952

반응식

HRID 10952 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]1

참가 물질

4

반응물 2

HCID 87949Lawesson's reagentHCID 10888648tert-Butyl 5-oxo-L-prolinate

생성물 1

HCID 14416882tert-Butyl (S)-5-thioxo-2-pyrrolidinecarboxylate수율 191.1%

시약·촉매·용매 1

HCID 241Benzene용매

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

  1. temperatureat reflux for 15.5 h
  2. concentrationconcentrated
  3. 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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