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tert-Butanol → (S)-tert-butyl 5-(4-chlorophenyl)-6-(1,1,1-trifluoropropan-2-yloxy)pyridin-3-ylcarbamate

HRID 1958146
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HRID 1958146 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([O:17][C@@H:18]([CH3:23])[C:19]([F:22])([F:21])[F:20])=[N:10][CH:11]=[C:12]([CH:16]=2)C(O)=O)=[CH:4][CH:3]=1.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:31])=CC=1.C([N:43]([CH2:46]C)CC)C.[C:48]([OH:52])([CH3:51])([CH3:50])[CH3:49]>>[C:48]([O:52][C:46](=[O:31])[NH:43][C:12]1[CH:11]=[N:10][C:9]([O:17][C@@H:18]([CH3:23])[C:19]([F:22])([F:21])[F:20])=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:16]=1)([CH3:51])([CH3:50])[CH3:49]
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5

반응물 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 66678484(S)-5-(4-Chlorophenyl)-6-(1,1,1-trifluoropropan-2-yloxy)nicotinic acid

생성물 1

HCID 67281043(S)-tert-butyl 5-(4-chlorophenyl)-6-(1,1,1-trifluoropropan-2-yloxy)pyridin-3-ylcarbamate수율 99%

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온도
100 °C

실험 절차

(S)-5-(4-Chlorophenyl)-6-(1,1,1-trifluoropropan-2-yloxy)nicotinic acid (0.300 g, 868 μmol) was suspended in t-butanol (3.0 mL). DPPA (358 mg, 282 μl), and triethylamine (87.8 mg, 120 μl, 868 μmol) were added and the reaction mixture was stirred at 100° C. overnight. The mixture was cooled to room temperature, extracted with ethyl acetate and sodium carbonate solution, the organic phase was dried with MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 20 g, 5% to 25% ethyl acetate in heptane) to give 0.36 g (99%) of the title compound as white solid; MS (EI) 417.3 (M+H)+.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate and sodium carbonate solution
  3. dry with materialthe organic phase was dried with MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by flash chromatography (silica gel, 20 g, 5% to 25% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-940d3428f1d741f0a4eb9775b1b38a38
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08410107B2

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