Iodoacetic Acid → HCID 11006035, Verbindung

HRID 225518

Reaktionsgleichung

Reaktionsgleichung von HRID 225518
C1CCC(N=C=NC2CCCCC2)CC1.[I:16][CH2:17][C:18]([OH:20])=[O:19].[CH:21]([O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]#[C:32][C:33]2[CH:38]=[C:37]([O:39][CH3:40])[C:36]([O:41][CH:42]([CH3:44])[CH3:43])=[CH:35][C:34]=2O)=[CH:27][C:26]=1[O:46][CH3:47])([CH3:23])[CH3:22]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[I:16][CH2:17][C:18]([O:20][C:29]1[CH:30]=[C:25]([O:24][CH:21]([CH3:22])[CH3:23])[C:26]([O:46][CH3:47])=[CH:27][C:28]=1[C:31]#[C:32][C:33]1[CH:34]=[CH:35][C:36]([O:41][CH:42]([CH3:44])[CH3:43])=[C:37]([O:39][CH3:40])[CH:38]=1)=[O:19]

Komponenten

6

Edukt 3

HCID 5240Iodoacetic AcidHCID 10868DicyclohexylcarbodiimideHCID 21923143HCID 21923143, Verbindung

Produkt 1

HCID 11006035HCID 11006035, VerbindungAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
18 °C

Versuchsvorschrift

DCC (1.60 g, 7.75 mmol) was added to a solution of 2-iodoacetic acid (1.44 g, 7.74 mmol), 2-[(4-isopropoxy-3-methoxy-phenyl)ethynyl]-5-isopropoxy-4-methoxyphenol (2.6 g, 7.03 mmol)and DMAP (43 mg, 0.35 mmol) in CH2Cl2 (30 mL) and the solution thereby obtained was stirred at 18° C. for 3 h. The resulting suspension was filtered (CH2Cl2 rinse) and the filtrate concentrated under reduced pressure. The residue was suspended in ether (30 mL) at 0° C. with rapid stirring then filtered [rinsing with Et2O (20 mL) pre-cooled at 0° C.] giving the title compound (3.67 g, 97%) as a cream solid mp 127-8° C. IR (KBr disc, cm−1) 2969, 2930, 2833, 1755, 1611, 1575, 1516, 1467, 1416, 1402, 1385, 1365, 1320, 1252, 1236, 1212, 1135, 1108. 1H NMR (300 MHz, CDCl3) δ 7.08 (dd, J=1.8, 8.4 Hz, 1H), 7.04 (d, J=2.1 Hz, 1H), 7.01 (s, 1H), 6.82 (d, J=8.4 Hz, 1H), 6.65 (s, 1H), 4.53 (septet, J=6.0 Hz, 2 Hz), 3.95 (s, 2H), 3.85 (s, 6H), 1.38 (d, J=6.0 Hz, 6H), 1.37 (d, J=6.0 Hz, 6H). 13C NMR+APT (75.5 MHz, CDCl3) δ 167.3 (C), 150.0 (C), 148.4 (C), 148.3 (C), 148.2 (C), 145.1 (C), 125.2 (CH), 115.6 (C), 115.3 (CH), 115.2 (CH), 115.0 (CH), 108.8 (CH), 93.6 (C), 82.7 (C), 72.0 (CH), 71.6 (CH), 56.5 (CH3), 56.3 (CH3), 22.3 (CH3), 22.0 (CH3), −6.2 (CH2). MS (70 eV) m/z (%): 538 (80, M+·), 496 (10, M+·-CH2CHCH3), 370 (10, M+·-CH2ICO), 328 (34), 286 (100); HRMS calcd for C24H27O6I 538.0852. Found 538.0854.

Aufarbeitung

  1. customthe solution thereby obtained
  2. filtrationThe resulting suspension was filtered
  3. wash(CH2Cl2 rinse)
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customwas suspended in ether (30 mL) at 0° C.
  6. stirringwith rapid stirring
  7. filtrationthen filtered
  8. wash[rinsing with Et2O (20 mL) pre-cooled at 0° C.]

Quellen und Nachweise

ORD-Eintrag
ord-ab9cd7a1a13f46d6af933c89d636ea68
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557118B2

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