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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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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
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HRID 2357099 반응식
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
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참가 물질

6

반응물 4

HCID 8900HeptaneHCID 87949Lawesson's reagentHCID 516892Sodium BicarbonateHCID 53349361HCID 53349361, 화합물

생성물 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-carboxylate수율 75.3%

시약·촉매·용매 1

HCID 1140
Toluene
용매

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온도
20.5 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-933497eeb29546d08273ba59cb2e9447
출처 데이터셋
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07759370B2

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