Nitrogen → {2'-[3-(3,4,5-Trihydroxy-phenyl)-propionylamino]-biphenyl-3-yl}-acetic acid methyl ester

HRID 383604

Reaktionsgleichung

Reaktionsgleichung von HRID 383604
N#N.[CH3:3][O:4][C:5](=[O:36])[CH2:6][C:7]1[CH:8]=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[NH:19][C:20](=[O:35])[CH2:21][CH2:22][C:23]2[CH:28]=[C:27]([O:29]C)[C:26]([O:31]C)=[C:25]([O:33]C)[CH:24]=2)[CH:10]=[CH:11][CH:12]=1.B(Br)(Br)Br>C(Cl)Cl>[CH3:3][O:4][C:5](=[O:36])[CH2:6][C:7]1[CH:8]=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[NH:19][C:20](=[O:35])[CH2:21][CH2:22][C:23]2[CH:24]=[C:25]([OH:33])[C:26]([OH:31])=[C:27]([OH:29])[CH:28]=2)[CH:10]=[CH:11][CH:12]=1

Komponenten

5

Edukt 3

HCID 947NitrogenHCID 25134Boron tribromideHCID 16116560{2'-[3-(3,4,5-Trimethoxy-phenyl)-propionylamino]-biphenyl-3-yl}-acetic acid methyl ester

Produkt 1

HCID 59819846{2'-[3-(3,4,5-Trihydroxy-phenyl)-propionylamino]-biphenyl-3-yl}-acetic acid methyl esterAusbeute 5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

(The following reaction is done in an anhydrous N2 atmosphere.) Dissolve {2′-[3-(3,4,5-Trimethoxy-phenyl)-propionylamino]-biphenyl-3-yl}-acetic acid methyl ester (72) (46 mg, 0.10 mmol) in anhydrous DCM (1.0 mL), cool the solution to −78° C. and add dropwise BBr3 (85 μL, 0.90 mmol). Stir the reaction mixture for 30 min at −78° C. and after slowly warming up for additional 2 h at rt. Add dropwise ice water, separate layers and extract aqu. layer with DCM (3 times). Wash combined organic layer with brine and dry with Na2SO4. Purify the crude product by preparative RP HPLC (gradient, water/CH3CN 95:5 to 5:95) to obtain {2′-[3-(3,4,5-Trihydroxy-phenyl)-propionylamino]-biphenyl-3-yl}-acetic acid methyl ester (73) (2 mg, 5%). 1H NMR (400 MHz, CD3CN): 2.43 (t, 2H, J=7.6 Hz); 2.69 (t, 2H, J=7.6 Hz); 3.66 (s, 3H); 3.70 (s, 2H); 6.25 (s, 2H); 7.18-7.34 (m, 5 H); 7.35-7.44 (m, 2H); 7.65 (br.s, 1H); 7.89 (br.d, 1H, J=8.3 Hz).

Aufarbeitung

  1. custom(The following reaction
  2. temperatureafter slowly warming up for additional 2 h at rt
  3. customseparate layers
  4. extractionextract aqu
  5. washWash
  6. dry with materialdry with Na2SO4
  7. customPurify the crude product by preparative RP HPLC (gradient, water/CH3CN 95:5 to 5:95)

Quellen und Nachweise

ORD-Eintrag
ord-a9dcd5bfeff7454cb3cd57ea2b25269b
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367677B2

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