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Lawesson's reagent → (S)-t-Butyl 2-(5-((3,4-dimethoxyphenoxy)methyl)-1,3,4-thiadiazol-2-yl)pyrrolidine-1-carboxylate

HRID 710058
ノート
印刷プレビュー

反応式

HRID 710058 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[O:6][CH2:7][C:8]([NH:10][NH:11][C:12]([C@@H:14]1[CH2:18][CH2:17][CH2:16][N:15]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=O)=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:40])=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[O:6][CH2:7][C:8]1[S:40][C:12]([C@@H:14]2[CH2:18][CH2:17][CH2:16][N:15]2[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[N:11][N:10]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 87949Lawesson's reagentHCID 86706750(S)-t-Butyl 2-(2-(2-(3,4-dimethoxyphenoxy)acetyl)hydrazinecarbonyl)pyrrolidine-1-carboxylate

生成物 1

HCID 86706771(S)-t-Butyl 2-(5-((3,4-dimethoxyphenoxy)methyl)-1,3,4-thiadiazol-2-yl)pyrrolidine-1-carboxylate収率 54.1%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

To a toluene (30 ml) solution of the compound (540 mg) obtained in Example 8-(1), Lawesson's reagent (750 mg) was added and the mixture was stirred at 90° C. for 6 hours. After adding water, extraction was conducted with AcOEt. The solvent was distilled off under reduced pressure and the residue was purified by silica gel chromatography (AcOEt/hexane) to give the titled compound (291 mg).

後処理

  1. additionAfter adding
  2. extractionwater, extraction
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was purified by silica gel chromatography (AcOEt/hexane)

出典と根拠

ORDレコード
ord-d87a05b49c254b14b001469273645b3a
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09181229B2

反応ノート

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