N,N-Dimethylaniline → Tert-butyl 3-(4-((2'-((dimethylamino)carbonyl)biphenyl-3-yl)methoxy)phenyl)propanoate

HRID 2422299Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2422299
[C:1]([O:5][C:6]([CH2:8][CH2:9][C:10]1[CH:32]=[CH:31][C:13]([O:14][CH2:15][C:16]2[CH:17]=[C:18]([C:22]3[C:23]([C:28](O)=[O:29])=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:19]=[CH:20][CH:21]=2)=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:33][N:34](C)[C:35]1C=CC=CC=1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>C(OCC)(=O)C.C(=O)([O-])O.[Na+].CN(C)C=O>[CH3:33][N:34]([CH3:35])[C:28]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([CH2:15][O:14][C:13]2[CH:31]=[CH:32][C:10]([CH2:9][CH2:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:11][CH:12]=2)[CH:17]=1)=[O:29]

Komponenten

8

Edukt 4

HCID 949N,N-DimethylanilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 575418463'-[4-(2-Tert-butoxycarbonylethyl)phenoxymethyl]biphenyl-2-carboxylic acid

Produkt 1

HCID 23083025Tert-butyl 3-(4-((2'-((dimethylamino)carbonyl)biphenyl-3-yl)methoxy)phenyl)propanoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a mixture of 3′-[4-(2-tert-butoxycarbonylethyl)phenoxymethyl]biphenyl-2-carboxylic acid (0.24 g, 0.56 mmol), dimethylaniline (2M tetrahydrofuran solution, 0.42 mL, 0.84 mmol), 1-hydroxybenzotriazole monohydrate (0.13 g, 0.84 mmol) and N,N-dimethylformamide (6.0 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.16 g, 0.84 mmol) at room temperature with stirring, and the mixture was stirred at the same temperature for 12 hrs. The reaction mixture was diluted with ethyl acetate, saturated aqueous sodium hydrogen carbonate, washed successively with 5% aqueous potassium hydrogensulfate solution and saturated brine, dried (anhydrous magnesium sulfate), and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1-1/2) to give tert-butyl 3-(4-((2′-((dimethylamino)carbonyl)biphenyl-3-yl)methoxy)phenyl)propanoate as a colorless oil. This compound was dissolved in trifluoroacetic acid (2 mL), and the mixture was stirred at room temperature for 1 hr, and concentrated under reduced pressure. The residue was purified by preparative HPLC (gradient cycle A) to give the title compound (58 mg, yield 26%) as colorless crystals. MS (APCI−): 402 (M−H).

Aufarbeitung

  1. stirringthe mixture was stirred at the same temperature for 12 hrs
  2. washwashed successively with 5% aqueous potassium hydrogensulfate solution and saturated brine
  3. dry with materialdried (anhydrous magnesium sulfate)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1-1/2)

Quellen und Nachweise

ORD-Eintrag
ord-300ac28a1de34807ba6fd9670e21b910
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960369B2

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