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Triphosgene → Tert-butyl (1-(4'-fluoro-4-nitrobiphenyl-3-ylcarbamoyl)azetidin-3-yl)methylcarbamate

HRID 62705
ノート
印刷プレビュー

反応式

HRID 62705 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[C:10]([NH2:17])[CH:9]=2)=[CH:4][CH:3]=1.Cl[C:19](Cl)([O:21]C(=O)OC(Cl)(Cl)Cl)Cl.[NH:30]1[CH2:33][CH:32]([CH2:34][NH:35][C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])[CH2:31]1>C(Cl)Cl.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[C:38]([O:37][C:36](=[O:42])[NH:35][CH2:34][CH:32]1[CH2:33][N:30]([C:19](=[O:21])[NH:17][C:10]2[CH:9]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH:13]=[CH:12][C:11]=2[N+:14]([O-:16])=[O:15])[CH2:31]1)([CH3:39])([CH3:41])[CH3:40]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 94429TriphosgeneHCID 15346872tert-butyl N-(azetidin-3-ylmethyl)carbamateHCID 71818257[1,1'-Biphenyl]-3-amine, 4'-fluoro-4-nitro-

生成物 1

HCID 71007318Tert-butyl (1-(4'-fluoro-4-nitrobiphenyl-3-ylcarbamoyl)azetidin-3-yl)methylcarbamate収率 69.7%

試薬・触媒・溶媒 2

HCID 311Citric Acid溶媒
HCID 6344
Dichloromethane
溶媒

実験手順

To a solution of 4′-fluoro-4-nitro-[1,1′-biphenyl]-3-amine (1.5 g, 6.46 mmol) in DCM (50 mL) were added triphosgene (1.917 g, 6.46 mmol) and TEA (8.5 g, 84 mmol) at 0° C. The reaction mixture was stirred at room temperature for two hours. tert-butyl azetidin-3-ylmethylcarbamate (1.203 g, 6.46 mmol) was then added at 0° C. and the reaction mixture was stirred at room temperature for four hours. The reaction crude was diluted with saturated citric acid solution and extracted with DCM. The organic layer was washed with water, brine, dried over Na2SO4, filtered and concentrated to yield crude residue which was purified by column chromatography eluting with 30% EtOAc in Hexane to afford tert-butyl((1-((4′-fluoro-4-nitro-[1,1′-biphenyl]-3-yl)carbamoyl)azetidin-3-yl)methyl)carbamate (2 g, 69.7% yield).

後処理

  1. stirringthe reaction mixture was stirred at room temperature for four hours
  2. customThe reaction crude
  3. extractionextracted with DCM
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield crude residue which
  9. customwas purified by column chromatography
  10. washeluting with 30% EtOAc in Hexane

出典と根拠

ORDレコード
ord-803b27dd5bef424dae76ae18aee9c735
出典データセット
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09447030B2

反応ノート

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