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

HRID 1958146
ノート
印刷プレビュー

反応式

HRID 1958146 の反応式
[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]
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

5

反応物 4

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

生成物 1

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

反応条件

温度
100 °C

実験手順

(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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-940d3428f1d741f0a4eb9775b1b38a38
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08410107B2

反応ノート

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