(Diethylamino)sulfur trifluoride → 8-(2-Chloro-benzenesulfonyl)-2-[4-(3-fluoro-oxetan-3-yl)-phenyl]-2,8-diaza-spiro[4.5]decan-1-one

HRID 2194208

반응식

HRID 2194208 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[CH2:32][CH2:31][C:14]2([C:18](=[O:19])[N:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]4(O)[CH2:29][O:28][CH2:27]4)=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)[CH2:13][CH2:12]1)(=[O:10])=[O:9].CCN(S(F)(F)[F:39])CC>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[CH2:32][CH2:31][C:14]2([C:18](=[O:19])[N:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]4([F:39])[CH2:29][O:28][CH2:27]4)=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)[CH2:13][CH2:12]1)(=[O:10])=[O:9]

참가 물질

4

반응물 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 595779078-(2-Chloro-benzenesulfonyl)-2-[4-(3-hydroxy-oxetan-3-yl)-phenyl]-2,8-diaza-spiro[4.5]decan-1-one

생성물 1

HCID 595780668-(2-Chloro-benzenesulfonyl)-2-[4-(3-fluoro-oxetan-3-yl)-phenyl]-2,8-diaza-spiro[4.5]decan-1-one수율 41.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-78 °C

실험 절차

To a solution of 8-(2-chloro-benzenesulfonyl)-2-[4-(3-hydroxy-oxetan-3-yl)-phenyl]-2,8-diaza-spiro[4.5]decan-1-one (described in example 229, 35 mg, 0.07 mmol) in DCM was added DAST (11 uL, 0.08 mmol) at −78° C. The reaction mixture was stirred at −78° C. for 3 hr and then quenched with sat. NaHCO3. The reaction mixture was diluted with DCM and washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to give a crude residue which was purified by flash column chromatography (1:1 AcOEt/heptane) to give 8-(2-chloro-benzenesulfonyl)-2-[4-(3-fluoro-oxetan-3-yl)-phenyl]-2,8-diaza-spiro[4.5]decan-1-one (14 mg, 40%) as a white solid. MS (ESI): 479.1 (MH+).

후처리

  1. customquenched with sat. NaHCO3
  2. additionThe reaction mixture was diluted with DCM
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a crude residue which
  8. customwas purified by flash column chromatography (1:1 AcOEt/heptane)

출처 및 근거

ORD 기록
ord-b72f92127bc846ceb01632654226e47a
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08329904B2

연결된 노트

불러오는 중…