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Heptane → (R)-tert-Butyl 2,2,4-trimethyl-4-(5-(4-(octyloxy)-3-(trifluoromethyl)phenyl)-1,3,4-thiadiazol-2-yl)oxazolidine-3-carboxylate

HRID 2357099
ノート
印刷プレビュー

反応式

HRID 2357099 の反応式
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[CH3:23][C:24]1([CH3:62])[N:28]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C@:27]([CH3:61])([C:36]([NH:38][NH:39][C:40](=O)[C:41]2[CH:46]=[CH:45][C:44]([O:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])=[C:43]([C:56]([F:59])([F:58])[F:57])[CH:42]=2)=O)[CH2:26][O:25]1.C([O-])(O)=O.[Na+].CCCCCCC>C1(C)C=CC=CC=1>[CH3:23][C:24]1([CH3:62])[N:28]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C@@:27]([CH3:61])([C:36]2[S:10][C:40]([C:41]3[CH:46]=[CH:45][C:44]([O:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])=[C:43]([C:56]([F:59])([F:58])[F:57])[CH:42]=3)=[N:39][N:38]=2)[CH2:26][O:25]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

6

反応物 4

HCID 8900HeptaneHCID 87949Lawesson's reagentHCID 516892Sodium BicarbonateHCID 53349361HCID 53349361、化合物

生成物 1

HCID 59384428(R)-tert-Butyl 2,2,4-trimethyl-4-(5-(4-(octyloxy)-3-(trifluoromethyl)phenyl)-1,3,4-thiadiazol-2-yl)oxazolidine-3-carboxylate収率 75.3%

試薬・触媒・溶媒 1

HCID 1140
Toluene
溶媒

反応条件

温度
20.5 °C

実験手順

A 12 L, round bottom flask was inerted and charged with Lawesson's reagent (211.5 g, 0.52 mol, 1.2 equiv), a solution of (S)-tert-butyl 2,2,4-trimethyl-4-(2-(4-(octyloxy)-3-(trifluoromethyl)benzoyl)-hydrazinecarbonyl)oxazolidine-3-carboxylate (D8A) (250 g—based on theoretical output, 0.43 mol) in toluene (2.5 L), and the resulting slurry was heated to 80° C. and held for 3 hours. TLC indicated the reaction was complete. The mixture was cooled to 18-23° C., charged with saturated NaHCO3 solution (2 L), which was slightly exothermic. The aqueous was extracted twice with ethyl acetate (2 L, 1.5 L), the organic phases were combined, concentrated, dissolved in dichloromethane (500 mL), charged with silica-gel (500 g), concentrated to remove dichloromethane, and purified using a silica-gel (2.5 kg) column which was eluted with 5% ethyl acetate: 95% heptane to afford the title product (185 g, 74% yield, 95% AUC by HPLC) as a yellow color oil.

後処理

  1. extractionThe aqueous was extracted twice with ethyl acetate (2 L, 1.5 L)
  2. concentrationconcentrated
  3. dissolutiondissolved in dichloromethane (500 mL)
  4. additioncharged with silica-gel (500 g)
  5. concentrationconcentrated
  6. customto remove dichloromethane
  7. custompurified
  8. washwas eluted with 5% ethyl acetate

出典と根拠

ORDレコード
ord-933497eeb29546d08273ba59cb2e9447
出典データセット
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07759370B2

反応ノート

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