2-Furanpropionic acid → HCID 46207593, Verbindung

HRID 388172

Reaktionsgleichung

Reaktionsgleichung von HRID 388172
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][C:8]([OH:10])=O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.C(N(CC)C(C)C)(C)C.[CH3:38][C:39]([CH3:59])=[CH:40][CH2:41][CH2:42]/[C:43](/[CH3:58])=[CH:44]/[CH2:45][CH2:46]/[C:47](/[CH3:57])=[CH:48]/[CH2:49][S:50][CH2:51][C@H:52]([NH2:56])[C:53]([OH:55])=[O:54]>C(Cl)Cl.C(OCC)(=O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][C:8]([NH:56][C@@H:52]([CH2:51][S:50][CH2:49]/[CH:48]=[C:47](\[CH3:57])/[CH2:46][CH2:45]/[CH:44]=[C:43](\[CH3:58])/[CH2:42][CH2:41][CH:40]=[C:39]([CH3:59])[CH3:38])[C:53]([OH:55])=[O:54])=[O:10]

Komponenten

7

Edukt 4

HCID 702862-Furanpropionic acidHCID 81531DiisopropylethylamineHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 6438372Farnesylcysteine

Produkt 1

HCID 46207593HCID 46207593, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 3-(2-furyl) propionic acid (168 mg, 1.2 mmol) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMTMM, 332 mg, 1.2 mmol) in CH2Cl2 (5 mL) was added N,N-diisopropyl-ethyl-amine (0.52 mL, 3 mmol). After stirring for 10 min, S-trans, trans-farnesyl-L-cysteine (325 mg, 1 mmol) was added slowly. The solution was stirred at room temperature overnight and then diluted with ethyl acetate (60 mL). The solution was washed by 0.5 N HCl (10 mL×1), H2O (10 mL×1) and brine (10 mL×1). The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by preparative HPLC (333 mg, 74%) to yield Compound N-96. 1H-NMR (500 MHz, CD3OD): δ 1.50 (s, 6H), 1.57 (s, 3H), 1.59 (s, 3H), 1.86-1.89 (m, 2H), 1.95-2.06 (m, 6H), 2.51 (t, J=8.0 Hz, 2H), 2.57-2.62 (m, 1H), 2.83-2.869 (m, 3H), 3.05 (dd, J=7.5, 13.5 Hz, 1H), 3.12-3.16 (m, 1H), 4.49 (dd, J=4.5, 8.0 Hz, 1H), 4.99-5.01 (m, 2H), 5.13 (t, J=7.5 Hz, 1H). 13C-NMR (125 MHz, CD3OD): δ 16.15, 16.24, 17.80, 24.96, 25.95, 27.39, 27.79, 30.11, 33.41, 35.08, 40.79, 40.89, 53.30, 106.28, 111.19, 121.61, 125.14, 125.46, 132.12, 136.27, 140.49, 142.36, 155.72, 174.00, 174.78; ES-MS: mass calcd for Chemical Formula: C25H37NO4S 447.63. Found (M+1) m/z 448.3, (M+23) m/z 470.2.

Aufarbeitung

  1. stirringThe solution was stirred at room temperature overnight
  2. washThe solution was washed by 0.5 N HCl (10 mL×1), H2O (10 mL×1) and brine (10 mL×1)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative HPLC (333 mg, 74%)
  6. customto yield Compound N-96

Quellen und Nachweise

ORD-Eintrag
ord-b78ac4a4684a431d864b0ebed8096803
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372884B2

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