Azetidine → (S)-ethyl 2-(2-(azetidin-1-yl)-5-methyl-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)-2-tert-butoxyacetate

HRID 879262ノート

反応式

HRID 879262 の反応式
Br[C:2]1[S:3][C:4]2[C:10]([O:11][S:12]([C:15]([F:18])([F:17])[F:16])(=[O:14])=[O:13])=[C:9]([C@H:19]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:8]([CH3:30])=[CH:7][C:5]=2[N:6]=1.[NH:31]1[CH2:34][CH2:33][CH2:32]1.[NH4+].[Cl-]>C1COCC1>[N:31]1([C:2]2[S:3][C:4]3[C:10]([O:11][S:12]([C:15]([F:17])([F:16])[F:18])(=[O:14])=[O:13])=[C:9]([C@H:19]([O:25][C:26]([CH3:28])([CH3:29])[CH3:27])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:8]([CH3:30])=[CH:7][C:5]=3[N:6]=2)[CH2:34][CH2:33][CH2:32]1

参加物

5

反応物 3

HCID 10422AzetidineHCID 25517Ammonium ChlorideHCID 86699785(S)-ethyl 2-(2-bromo-5-methyl-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)-2-tert-butoxyacetate

生成物 1

HCID 86699784(S)-ethyl 2-(2-(azetidin-1-yl)-5-methyl-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)-2-tert-butoxyacetate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

To a solution of 32 (50 mg, 0.094 mmol) in THF (1 mL) was added azetidine (20 μL). The reaction mixture was heated at 70° C. for 30 min. A saturated solution of NH4Cl (3 mL) was added, and the layers were separated. The aqueous layer was extracted with EtOAc. The combined organic layer were dried, filtered, and concentrated in vacuo. The crude material was purified by column chromatography (EtOAc/hexanes) to give 38 mg of 33. LCMS-ESI+: calc'd for C20H25F3N2O6S2: 511.1 (M+H+); Found: 511.0 (M+H+).

後処理

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with EtOAc
  3. customThe combined organic layer were dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by column chromatography (EtOAc/hexanes)

出典と根拠

ORDレコード
ord-b8da5846c1824b32870a9c1f3ef69bd3
出典データセット
uspto-grants-2015_03
特許番号
US08987250B2

反応ノート

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