Dicyclohexylcarbodiimide → HCID 86628344, Verbindung

HRID 1808269

Reaktionsgleichung

Reaktionsgleichung von HRID 1808269
OC[CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][N:9]([CH3:17])[C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13].[C:18]([O:27][CH3:28])(=[O:26])[CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O-:25])=[O:24].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:18]([O:27][CH3:28])(=[O:26])[CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][N:9]([CH3:17])[C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:24]

Komponenten

6

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 6994472Methyl adipateHCID 86628343Tert-butyl 2-(3-hydroxypropoxy)ethoxy(methyl)carbamate

Produkt 1

HCID 86628344HCID 86628344, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 2-(3-hydroxypropoxy)ethoxy(methyl)carbamate (152 mg, 0.646 mmol) and monomethyl adipate (104 mg, 0.646 mmol) in CH2Cl2 (4 mL) were added DCC (146 mg, 0.711 mmol) and DMAP (16 mg, 0.129 mmol). The reaction mixture was stirred at room temperature for 16 h and filtered. The solvent was removed under reduced pressure. The crude product was purified by silica gel flash column chromatography using 27% EtOAc/hexanes as eluent. The desired product was obtained as colorless oil (152 mg, 0.403 mmol, 62%). 1H NMR (CDCl3, 400 MHz): δ (ppm) 1.41 (s, 9 H), 1.56-1.60 (m, 4 H), 2.25-2.27 (m, 4 H), 3.03 (s, 3 H), 3.58 (s, 3 H), 3.59-3.63 (m, 4 H), 3.91-3.94 (m, 2 H), 4.14-4.16 (m, 2 H).

Aufarbeitung

  1. filtrationfiltered
  2. customThe solvent was removed under reduced pressure
  3. customThe crude product was purified by silica gel flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-01d1cd904c6f409a9c03e09626af867f
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08357777B2

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