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(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
ノート
印刷プレビュー

反応式

HRID 2194208 の反応式
[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]
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

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-b72f92127bc846ceb01632654226e47a
出典データセット
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08329904B2

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