Diisopropylethylamine → 4-((t-Butoxycarbonyl)(methyl)amino)-4'-(((2-methoxy-1-((methylamino)carbonyl)-2-oxoethyl)(methyl)amino)carbonyl)biphenyl

HRID 1519667Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1519667
Cl.[CH3:2][NH:3][C:4](=[O:12])[C@H:5]([C:8](=[O:11])[O:9][CH3:10])[NH:6][CH3:7].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[C:46]([O:50][C:51]([N:53]([CH3:69])[C:54]1[CH:59]=[CH:58][C:57]([C:60]2[CH:65]=[CH:64][C:63]([C:66](O)=[O:67])=[CH:62][CH:61]=2)=[CH:56][CH:55]=1)=[O:52])([CH3:49])([CH3:48])[CH3:47]>O.C(OCC)(=O)C.CN(C=O)C>[C:46]([O:50][C:51]([N:53]([CH3:69])[C:54]1[CH:59]=[CH:58][C:57]([C:60]2[CH:65]=[CH:64][C:63]([C:66]([N:6]([CH:5]([C:4]([NH:3][CH3:2])=[O:12])[C:8]([O:9][CH3:10])=[O:11])[CH3:7])=[O:67])=[CH:62][CH:61]=2)=[CH:56][CH:55]=1)=[O:52])([CH3:47])([CH3:48])[CH3:49]

Komponenten

8

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 712682544'-((t-Butoxycarbonyl)(methyl)amino)biphenyl-4-carboxylic acidHCID 86679246N,N2,O-trimethyl-3-oxoserinamide hydrochloride2×

Produkt 1

HCID 712682134-((t-Butoxycarbonyl)(methyl)amino)-4'-(((2-methoxy-1-((methylamino)carbonyl)-2-oxoethyl)(methyl)amino)carbonyl)biphenylAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

N,N2,O-trimethyl-3-oxoserinamide hydrochloride (Intermediate 5-2, 90 mg), HATU (0.17 g) and DIPEA (0.16 mL) were added to a DMF (2.0 mL) solution of 4′-((t-butoxycarbonyl)(methyl)amino)biphenyl-4-carboxylic acid (0.10 g), as obtained in Example 2-(2), and the mixture was stirred for 16 hours at room temperature. Ethyl acetate and water were added to the reaction mixture to isolate the organic layer, and the extract was washed sequentially with water and brine. The system was dried over anhydrous sodium sulfate and, after separation of the desiccant by filtration, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/3) to obtain 4-((t-butoxycarbonyl)(methyl)amino)-4′-(((2-methoxy-1-((methylamino)carbonyl)-2-oxoethyl)(methyl)amino)carbonyl)biphenyl (white foam) (73 mg, 51%).

Aufarbeitung

  1. customto isolate the organic layer
  2. washthe extract was washed sequentially with water and brine
  3. dry with materialThe system was dried over anhydrous sodium sulfate
  4. customafter separation of the
  5. filtrationdesiccant by filtration
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/3)

Quellen und Nachweise

ORD-Eintrag
ord-4a328d5ec0564b43ab762dfde2cd9f1b
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073821B2

Notizen zur Reaktion

Wird geladen…