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

HRID 10952

反応式

HRID 10952 の反応式
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

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

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

  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)

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

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