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N-(2,2,2-Trifluoroethylidene)-4-methoxyaniline → Tert-butyl 5-chloro-2-{2-[(4-methoxyphenyl)amino]-3,3,3-trifluoropropyl}benzylcarbamate

HRID 1058250
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1058250
C([Li])(CC)C.[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([CH3:22])=[C:11]([CH:21]=1)[CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17].[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]=[CH:32][C:33]([F:36])([F:35])[F:34])=[CH:27][CH:26]=1>C1COCC1>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:22][CH:32]([NH:31][C:28]2[CH:29]=[CH:30][C:25]([O:24][CH3:23])=[CH:26][CH:27]=2)[C:33]([F:35])([F:34])[F:36])=[C:11]([CH:21]=1)[CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19]
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Komponenten

5

Edukt 3

HCID 11030904N-(2,2,2-Trifluoroethylidene)-4-methoxyanilineHCID 18672379Tert-butyl 5-chloro-2-methylbenzylcarbamateHCID 178418400CID 53628100

Produkt 1

HCID 18672399Tert-butyl 5-chloro-2-{2-[(4-methoxyphenyl)amino]-3,3,3-trifluoropropyl}benzylcarbamateAusbeute 41,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

sec-Butyl-lithium (1.3 M in cyclohexane, 21.72 mL) was added to a stirred solution of tert-butyl 5-chloro-2-methylbenzylcarbamate (3.61 g, 14.12 mmol) in THF (30 mL) at −78° C. under nitrogen to give a deep red solution. After 10 min N-(4-methoxyphenyl)-N-(2,2,2-trifluoroethylidene)amine (3.01 g, 14.12 mmol) was added and after a further 5 min the solution was quenched with excess saturated aqueous NH4Cl and warmed to ambient temperature. The solution was partitioned between EtOAc and brine. The organic layer was dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash column chromatography on silica (eluting with 5% methylene chloride, 5-20% ethyl acetate/hexanes gradient) to give tert-butyl 5-chloro-2-{2-[(4-methoxyphenyl)amino]-3,3,3-trifluoropropyl}benzylcarbamate (2.69 g) as a gum; 1H NMR (CDCl3 400 MHz) δ 1.47 (s, 9H), 2.90 (dd, J=10.7 and 14.7 Hz, 1H), 3.16 (dd, J=3.4 and 14.7 Hz, 1H), 3.62 (br d, J=8.2 Hz, 1H), 3.71 (s, 3H), 4.03 (br m, 1H), 4.29 (dd, J=5.6 and 14.7 Hz, 1H), 4.34 (br dd, 1H), 4.87 (br s, 1H), 6.47 (d, J=8.9 Hz, 2H), 6.69 (d, J=8.9 Hz, 2H), 7.14 (d, J=8.2 Hz, 1H), 7.19 (dd, J=8.2 and 2.0 Hz, 1H), 7.23 (s, 1H).

Aufarbeitung

  1. customto give a deep red solution
  2. customwas quenched with excess saturated aqueous NH4Cl
  3. customThe solution was partitioned between EtOAc and brine
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. customevaporated in vacuo
  6. customThe residue was purified by flash column chromatography on silica (eluting with 5% methylene chloride, 5-20% ethyl acetate/hexanes gradient)

Quellen und Nachweise

ORD-Eintrag
ord-e865b0d3f6214fefaab9c35a42d1dd12
Quelldatensatz
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06515011B2

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