Sodium hydride → HCID 59820046, Verbindung

HRID 553570

Reaktionsgleichung

[OH:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[H-].[Na+].C1(C)C=CC(S(O[CH2:26][CH2:27][O:28][C@@H:29]2[CH2:34][CH2:33][CH2:32][C@H:31]([O:35][CH2:36][C:37]3[N:38]=[C:39]([C:43]4[CH:44]=[C:45]([CH3:49])[CH:46]=[CH:47][CH:48]=4)[O:40][C:41]=3[CH3:42])[CH2:30]2)(=O)=O)=CC=1>CN(C=O)C.[Na+].[Cl-].C(OCC)(=O)C>[CH3:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:2]([O:1][CH2:26][CH2:27][O:28][C@@H:29]2[CH2:34][CH2:33][CH2:32][C@H:31]([O:35][CH2:36][C:37]3[N:38]=[C:39]([C:43]4[CH:44]=[C:45]([CH3:49])[CH:46]=[CH:47][CH:48]=4)[O:40][C:41]=3[CH3:42])[CH2:30]2)[C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Komponenten

Reaktionsbedingungen

Temperatur: 40 °C

Versuchsvorschrift

90 mg of ethyl 2-hydroxy-6-methylbenzoate are dissolved in 2 ml of dry DMF, and 23 mg of a 60 percent strength sodium hydride suspension are added. After 30 min at room temperature, 100 mg of ((1R,3S)-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxy]ethyl toluene-4-sulfonate in 2 ml of DMF are added. The mixture is stirred at 40° C. until the reaction has gone to completion (monitored by LC-MS). After cooling, the mixture is diluted with sat. NaCl solution and ethyl acetate. The organic phase is dried over sodium sulfate and the solvent is removed under reduced pressure. This gives ethyl (1R,3S)-2-methyl-6-{2-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxy]ethoxy}benzoate as a yellowish oil. C30H37NO6 (507.63), MS (ESI): 508 (M+H+).

Aufarbeitung

temperatureAfter cooling
dry with materialThe organic phase is dried over sodium sulfate
customthe solvent is removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-f06fe5ff6da749bab460989d306cfb63
Quelldatensatz: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08048901B2

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