Dicyclohexylcarbodiimide → HCID 66843104, Verbindung

HRID 254088

Reaktionsgleichung

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH2:17][S:18][CH2:19][C:20](O)=[O:21])[O:14][CH2:13][C:12]([CH3:16])([CH3:15])[CH2:11][O:10]2)=[CH:5][CH:4]=1.C1(N=C=NC2CCCCC2)CCCCC1.[C:38]1([C@H:44]2[CH2:48][O:47][C:46](=[O:49])[NH:45]2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2([CH2:17][S:18][CH2:19][C:20]([N:45]3[C@@H:44]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[CH2:48][O:47][C:46]3=[O:49])=[O:21])[O:14][CH2:13][C:12]([CH3:16])([CH3:15])[CH2:11][O:10]2)=[CH:7][CH:8]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

({[2-(4-Methoxyphenyl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)acetic acid (5.4 g, 16.5 mmol) was dissolved in dry CH2Cl2 (80 ml) and cooled to 0° C. N,N′-dicyclohexylcarbodiimide (DCC, 3.76 g; 18.2 mmol) in 20 ml of CH2Cl2 and 4-(dimethylamino)pyridine (DMAP, 4.04 g, 33.1 mmol) were added and the mixture was stirred at 0° C. for 30 minutes. (S)-(+)-4-Phenyl-2-oxazolidinone (2.69 g, 16.5 mmol) was added and the mixture was stirred at room temperature for 17 h. The mixture was filtered, concentrated under reduced pressure and purified by flash-chromatography (hexane:EtOAc 4:1 then 2:1). This afforded 5.69 g (73%) of the title compound as a white solid. 1H-NMR (CDCl3, 200 MHz): δ 0.6 (s, 3H), 1.3 (s, 3H), 2.8 (s, 2H), 3.4 (s, 4H), 3.8 (s, 2H), 3.8 (s, 3H), 4.3 (dd, 1H), 4.7 (t, 1H), 5.4 (dd, 1H), 6.9 (d, 2H), 7.3 (m, 7H).

Aufarbeitung

stirringthe mixture was stirred at room temperature for 17 h
filtrationThe mixture was filtered
concentrationconcentrated under reduced pressure
custompurified by flash-chromatography (hexane:EtOAc 4:1

Quellen und Nachweise

ORD-Eintrag: ord-abcfa00923de4b1cb8e133ee79f1aa82
Quelldatensatz: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07871998B2

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