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

HRID 1468702
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HRID 1468702 반응식
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
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5

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran
용매

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온도
70 °C

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-6f68696785614b2fa47fdfe8629939ca
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09006229B2

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