Dicyclohexylcarbodiimide → HCID 54213439, Verbindung

HRID 439878Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 439878
[O:1]1[CH:5]=[CH:4][C:3]([CH:6]([N:8]([OH:12])[C:9]([NH2:11])=[O:10])[CH3:7])=[CH:2]1.[CH3:13][C@H:14]([C:27](O)=[O:28])[C:15]1[CH:16]=[CH:17][C:18]2[CH:19]=[C:20]([O:25][CH3:26])[CH:21]=[CH:22][C:23]=2[CH:24]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[CH3:26][O:25][C:20]1[CH:19]=[C:18]2[C:23](=[CH:22][CH:21]=1)[CH:24]=[C:15]([C@H:14]([CH3:13])[C:27]([O:12][N:8]([CH:6]([C:3]1[CH:4]=[CH:5][O:1][CH:2]=1)[CH3:7])[C:9]([NH2:11])=[O:10])=[O:28])[CH:16]=[CH:17]2

Komponenten

5

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 130007N-1-(fur-3-ylethyl)-N-hydroxyureaHCID 156391Naproxen

Produkt 1

HCID 54213439HCID 54213439, VerbindungAusbeute 68,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of N-1-(fur-3-yl)ethyl-N-hydroxyurea (1.00 g, 5.9 mmol), prepared as described in U.S. Pat. No. 5,112,848, in CH2Cl2 (25 mL) was added naproxen (135 g, 5.9 mmol) followed by dicyclohexylcarbodiimide (1.34 g, 6.49 mmol), and a crystal of 4-N,N-dimethylaminopyridine. The reaction was stirred for 18 hours. The reaction mixture was filtered through Celite and the filtrate was concentrated in vacuo. The residue was purified by chromatography on silica gel (ether), followed by crystallization in ethyl acetate/hexanes to give N-[(S)-2-(6-methoxynaphth-2-yl)propionyloxy]-N-[1-(fur-3-yl)ethyl]urea (1.54 g). m.p. 128.5°-134° C. 1H NMR (300 MHz, DMSO-d6, mixture of diastereomers) δ 0.72 and 1.12 (bm, 3H), 1.48 (bm, 3H), 3.87 (s, 3H), 4.13 (bm, 1H), 5.14 (bm, 1H), 6.79 and 6.94 (bs, 2H), 7.16 (m, 2H), 7.29-7.46 (m, 3H), 7.69-7.86 (m, 3H). MS (DCI/NH3) m/e 383 (M+H)+. Analysis calc'd for C21H22N2O5 : C, 65.95; H, 5.80; N, 7.33. Found: C, 65.39; H; 5.80; N, 7.26.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by chromatography on silica gel (ether)
  4. customfollowed by crystallization in ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-bd02401f04754aee997b55f1a6417696
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05516789

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