Water → (2R)-2-amino-N-[5-{3-[(2-chloropyridin-4-yl)methyl]-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl}-2-(trifluoromethoxy)phenyl]-2-phenylacetamide

HRID 546571

Reaktionsgleichung

Reaktionsgleichung von HRID 546571
F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2N=N1.[CH2:23]([N:25](CC)CC)[CH3:24].[NH2:30][C:31]1[CH:32]=[C:33]([N:42]2[C:46](=[O:47])[C:45]([CH3:49])([CH3:48])[N:44]([CH2:50][C:51]3[CH:56]=[CH:55][N:54]=[C:53]([Cl:57])[CH:52]=3)[C:43]2=[O:58])[CH:34]=[CH:35][C:36]=1[O:37][C:38]([F:41])([F:40])[F:39].[OH2:59]>CN(C)C=O>[NH2:25][C@H:23]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:24]([NH:30][C:31]1[CH:32]=[C:33]([N:42]2[C:46](=[O:47])[C:45]([CH3:49])([CH3:48])[N:44]([CH2:50][C:51]3[CH:56]=[CH:55][N:54]=[C:53]([Cl:57])[CH:52]=3)[C:43]2=[O:58])[CH:34]=[CH:35][C:36]=1[O:37][C:38]([F:39])([F:40])[F:41])=[O:59]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 576260063-[3-Amino-4-(trifluoromethoxy)phenyl]-1-[(2-chloropyridin-4-yl)methyl]-5,5-dimethylimidazolidine-2,4-dione

Produkt 1

HCID 86629090(2R)-2-amino-N-[5-{3-[(2-chloropyridin-4-yl)methyl]-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl}-2-(trifluoromethoxy)phenyl]-2-phenylacetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 0.6 g of D-N-Boc-phenylglycine in 12 mL of dimethylformamide is added 0.74 g or O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU). After stirring for 5 minutes, 0.837 mL of triethylamine and 0.86 g of 3-[3-amino-4-(trifluoromethoxy)phenyl]-1-[(2-chloropyridin-4-yl)methyl]-5,5-dimethylimidazolidine-2,4-dione obtained in stage c) below are successively added. The reaction mixture is heated at 70° C. for 15 hours and then poured into 100 mL of water. The aqueous phase is extracted with three times 70 mL of ethyl acetate and the combined organic phases are washed with 50 mL of saturated sodium chloride solution, dried over magnesium sulphate, filtered and evaporated. The residue is purified by chromatography on a column of silica, eluting with a mixture of dichloromethane and ethyl acetate (70/30 by volume) to give 220 mg of (2R)-2-amino-N-[5-{3-[(2-chloropyridin-4-yl)methyl]-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl}-2-(trifluoromethoxy)phenyl]-2-phenylacetamide, the characteristics of which are as follows:

Aufarbeitung

  1. extractionThe aqueous phase is extracted with three times 70 mL of ethyl acetate
  2. washthe combined organic phases are washed with 50 mL of saturated sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is purified by chromatography on a column of silica
  7. washeluting with a mixture of dichloromethane and ethyl acetate (70/30 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-1cdef8915ae345ef922b3be0fca5f887
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935819B2

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