Potassium Carbonate → HCID 89814708, Verbindung

HRID 1496798Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1496798
C(OC(C[N:7]1[C:16](=[O:17])[CH:15]2[CH:10]([CH:11]3[C:18](=[C:19]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=4)[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:14]2[C:13]([C:32]([OH:45])([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:12]3)[C:8]1=[O:9])=O)C.[C:46]([O:52][CH2:53]Cl)(=[O:51])[C:47]([CH3:50])([CH3:49])[CH3:48].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[OH:45][C:32]([C:13]1[CH:14]2[C:18](=[C:19]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:11]([CH:12]=1)[CH:10]1[C:8]([N:7]([CH2:53][O:52][C:46](=[O:51])[C:47]([CH3:50])([CH3:49])[CH3:48])[C:16](=[O:17])[CH:15]21)=[O:9])([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 87885Chloromethyl pivalateHCID 89814504HCID 89814504, Verbindung

Produkt 1

HCID 89814708HCID 89814708, VerbindungAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A similar procedure (Hursthouse, M. B.; Khan, A.; Marson, C. M.; Porter, R. A. Tetrahedron Lett 1995, 36, 33, 5979-5982) to that described for the preparation of 207 was followed using NRB (200 mg, 0.39 mmol) in dimethylformamide (2 mL), chloromethyl pivalate (41) (59 mg, 0.39 mmol) in dimethylformamide (0.5 mL), and potassium carbonate (54 mg, 0.39 mmol). Purification by flash chromatography (hexane/ethyl acetate 1:1) afforded 8 as a colourless solid (118 mg, 0.19 mmol, 48%). mp 95-98° C.; 1H NMR (400 MHz, CDCl3) δ 1.18-1.19 (8.4H, m, tBu), 1.25-1.26 (0.6H, m, tBu), 3.38 (0.2H, dd, J=7.9 and 4.5 Hz, W/H-3), 3.45 (0.5H, dd, J=7.9 and 4.5 Hz, Y/H-3), 3.51-3.59 (0.4H, m, 0.2H U/H-2 and U/H-3, 0.2H V/H-2), 3.63-3.64 (0.2H, m, W/H-4), 3.67-3.76 (0.9H, m, 0.2H V/H-3, 0.2H W/H-2 and 0.5H Y/H-2), 3.88-3.92 (0.3H, m, 0.1H U/H-1 and 0.2H V/H-1), 4.00-4.01 (0.5H, dt, J=4.5 and 1.3 Hz, Y/H-4), 4.20-4.21 (0.1H, m, U/H-4), 4.35-4.36 (0.2H, dt, J=4.5 and 1.3 Hz, V/H-4), 4.49-4.52 (0.7H, m, 0.2H W/H-1 and 0.5H Y/H-1), 5.26-5.29 (0.7H, m, CH2), 5.31-5.62 (3H, m, 1.3H CH2, 0.2H V/H-6, 0.5H Y/H-6 and 1H OH), 6.04-6.06 (0.3H, m, 0.1H U/H-6 and 0.211 W/H-6), 6.71-7.57 (16H, m, Ar), 8.42-8.50 (0.6H, m, 0.2H 2U/αPyr and 0.4H 2VαPyr), 8.54-8.55 (0.7H, m, 0.2H W/αPyr and 0.5H Y/αPyr), 8.61-8.63 (0.7H, m, 0.2H W/αPyr and 0.5H Y/αPyr); vmax(nujol)/cm−1 1140 and 1212 (C—O ester), 1586 (C═O imide), 1715 (C═O ester); m/z (FAB+) 626 (MH+, 67%), 120 (100); (Found: MH+ 626.2644, C39H36N3O5 requires 626.2655).

Aufarbeitung

  1. customPurification by flash chromatography (hexane/ethyl acetate 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-b39289bce3e147a4ac4aca85aaafb66c
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09198420B2

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