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Triethylamine → HCID 178452054、化合物

HRID 556700
ノート
印刷プレビュー

反応式

HRID 556700 の反応式
[C:1]([C:5]1[S:9][C:8](=[NH:10])[N:7]([CH2:11][CH:12]2[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13]2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[F:30][C:31]1[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][C:32]=1[C:33](Cl)=[O:34]>O1CCCC1>[C:1]([C:5]1[S:9]/[C:8](=[N:10]\[C:33](=[O:34])[C:32]2[CH:36]=[C:37]([C:40]([F:41])([F:42])[F:43])[CH:38]=[CH:39][C:31]=2[F:30])/[N:7]([CH2:11][CH:12]2[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13]2)[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]
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 3

HCID 8471TriethylamineHCID 27348802-Fluoro-5-(trifluoromethyl)benzoyl ChlorideHCID 66660694tert-butyl 3-((5-tert-butyl-2-iminothiazol-3(2H)-yl)methyl)azetidine-1-carboxylate

生成物 1

HCID 178452054HCID 178452054、化合物収率 80%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

To a solution of the product of Example 42A (4.1 g, 12.5 mmol) in tetrahydrofuran (40 mL) was added triethylamine (5.2 mL, 37.6 mmol) followed by 2-fluoro-5-(trifluoromethyl)benzoyl chloride (2.0 mL, 13.2 mmol). This mixture was warmed to 50° C. and was allowed to stir for 90 min then the mixture was cooled to ambient temperature and was stirred for 16 h. The mixture was quenched with saturated, aqueous NH4Cl (20 mL) and diluted with ethyl acetate (20 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (3×10 mL). The combined organics were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude material was purified by column chromatography (SiO2, 60% hexanes in ethyl acetate) to give the title compound (5.2 g, 10.0 mmol, 80% yield). MS (DCI/NH3) m/z 516 (M+H)+.

後処理

  1. temperaturethe mixture was cooled to ambient temperature
  2. stirringwas stirred for 16 h
  3. customThe mixture was quenched with saturated, aqueous NH4Cl (20 mL)
  4. additiondiluted with ethyl acetate (20 mL)
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with ethyl acetate (3×10 mL)
  7. dry with materialThe combined organics were dried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude material was purified by column chromatography (SiO2, 60% hexanes in ethyl acetate)

出典と根拠

ORDレコード
ord-988091fe9c3a46e1a98f95c78efad551
出典データセット
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08058293B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート