Sodium hydride → HCID 178477657, Verbindung

HRID 518397

Reaktionsgleichung

[C@H]1(O)CC[C@H](O)CC1.[H-].[Na+].[Si]([O:18][CH:19]1[CH2:24][CH2:23][CH:22]([O:25][C:26]2[CH:31]=[CH:30][C:29]([S:32]([CH2:35][CH3:36])(=[O:34])=[O:33])=[CH:28][C:27]=2[C:37]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[C:40](=[O:47])[N:39]([CH3:48])[CH:38]=2)[CH2:21][CH2:20]1)(C(C)(C)C)(C)C>CN(C=O)C>[CH2:35]([S:32]([C:29]1[CH:30]=[CH:31][C:26]([O:25][C@H:22]2[CH2:21][CH2:20][C@H:19]([OH:18])[CH2:24][CH2:23]2)=[C:27]([C:37]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[C:40](=[O:47])[N:39]([CH3:48])[CH:38]=2)[CH:28]=1)(=[O:33])=[O:34])[CH3:36]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a solution of trans-1,4-cyclohexanediol (504.0 mg, 4.34 mmol) in anhydrous DMF (4 mL) was added NaH (139.0 mg, 3.47 mmol, 60% in mineral oil) at 0° C. and then stirred at 0° C. for 1 h. The compound from step 1 (100.0 mg, 0.29 mmol) was added. The mixture was stirred at 0° C. for 0.5 h and then at r.t. 18 hrs. It was then quenched with MeOH (4 mL) and filtered. The filtrate was purified by prep-HPLC to give the title compound (37.0 mg, 30.0%) as an off-white solid. 1H NMR (CDCl3, 40 MHz) δ 8.51 (d, J=7.6 Hz, 1H), 7.94 (dd, J1=8.8 Hz, J2=2.4 Hz, 1H), 7.83 (d, J=2.0 Hz, 1H), 7.56 (t, J=6.8 Hz, 1H), 7.51 (t, J=6.8 Hz, 1H), 7.16 (d, J=7.6 Hz, 1H), 7.11 (d, J=8.8 Hz, 1H), 7.05 (s, 1H), 4.43-4.18 (m, 1H), 3.67 (s, 3H), 3.65-3.62 (m, 1H), 3.16 (q, J=7.6 Hz, 2H), 2.00-1.90 (m, 2H), 1.71-1.65 (m, 2H), 1.42-1.30 (m, 7H). LCMS (M+H)+=442.0 (M+1)+

Aufarbeitung

stirringThe mixture was stirred at 0° C. for 0.5 h
customat r.t
custom18 hrs
customIt was then quenched with MeOH (4 mL)
filtrationfiltered
customThe filtrate was purified by prep-HPLC

Quellen und Nachweise

ORD-Eintrag: ord-779af6c04059428faf35fead176072cc
Quelldatensatz: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09115114B2

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