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Lawesson's reagent → (R)-tert-Butyl 2,2,4-trimethyl-4-(5-(4-(octyloxy)-3-(trifluoromethyl)phenyl)thiazol-2-yl)oxazolidine-3-carboxylate

HRID 2357061
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HRID 2357061 반응식
[CH3:1][C:2]1([CH3:40])[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@:5]([CH3:39])([C:14](=O)[NH:15][CH2:16][C:17]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[C:21]([C:34]([F:37])([F:36])[F:35])[CH:20]=2)=O)[CH2:4][O:3]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:50])=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:40])[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@:5]([CH3:39])([C:14]2[S:50][C:17]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[C:21]([C:34]([F:37])([F:36])[F:35])[CH:20]=3)=[CH:16][N:15]=2)[CH2:4][O:3]1
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HCID 87949Lawesson's reagentHCID 59384447(R)-tert-Butyl 2,2,4-trimethyl-4-(2-(4-(octyloxy)-3-(trifluoromethyl)phenyl)-2-oxoethylcarbamoyl)oxazolidine-3-carboxylate

생성물 1

HCID 59384295(R)-tert-Butyl 2,2,4-trimethyl-4-(5-(4-(octyloxy)-3-(trifluoromethyl)phenyl)thiazol-2-yl)oxazolidine-3-carboxylate수율 67%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
100 °C

실험 절차

A suspension of protected oxazolidine-amide 6 (180 mg, 1.0 equivalent) and Lawesson's Reagent (390 mg, 3.0 equivalents) in toluene (5 mL) was sealed and heated at 100° C. for 1 hour. After cooling to room temperature, the reaction mixture was purified by silica gel column chromatography using the Combi-Flash system (Hex:EtOAc) as a thick colourless oil in 67% yield (120 mg). TLC (1:2 EtOAc:Hex), Rf=0.8; MS (ESI, M+H+)=571.11; 1H NMR (400 MHz, CDCl3) δ 7.73 (br s, 1H), 7.70 (s, 1H), 7.61 (d, 1H, J=6.8 Hz), 7.01 (d, 1H, J=6.8 Hz), 3.96-4.28 (m, 4H), 1.21-1.99 (m, 30H), 0.89 (t, 3H, J=7.6 Hz).

후처리

  1. customwas sealed
  2. temperatureAfter cooling to room temperature
  3. customthe reaction mixture was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-e57b4c885fcb45c9a454ed8b99b6de68
출처 데이터셋
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07759370B2

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