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

HRID 2201712
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HRID 2201712 반응식
[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]
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참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 311Citric Acid용매
HCID 6344
Dichloromethane
용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6eba885f89024037b6bfc61a155ddf1c
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09365498B2

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