Potassium Carbonate → HCID 131734194, Verbindung

HRID 1496801Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1496801
[CH2:1]([O:3][C:4]([CH2:6][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:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].ClCC(O[CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62]CC)=O>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:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:11]([CH:12]=1)[CH:10]1[C:8]([N:7]([CH2:6][C:4]([O:3][CH2:1][CH2:2][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH3:62])=[O:5])[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:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 228762Octyl chloroacetateHCID 89814504HCID 89814504, Verbindung

Produkt 1

HCID 131734194HCID 131734194, VerbindungAusbeute 71 %

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 (0.37 g, 0.7 mmol) and potassium carbonate (0.25 g, 1.8 mmol) in dimethylformamide (5 mL), and octyl chloroacetate (0.32 g, 1.5 mmol) in dimethylformamide (2 mL), and the mixture stirred at room temperature for 2 h. Purification by flash chromatography (hexane/ethyl acetate 2:1) afforded 369 as a white solid (0.34 g, 0.5 mmol, 71%). 1H NMR (400 MHz, CDCl3) δ 0.87-0.90 (3H, m, O(CH2)7CH3), 1.26-1.30 (10H, m, OCH2CH2(CH2)5CH3), 1.61-1.63 (2H, m, OCH2CH2(CH2)5CH3), 3.40-4.56 (8H, m, OCH2(CH2)6CH3, NCH2, H-1, H-2, H-3, H-4), 5.48 (0.5H, s, OH), 5.52 (0.3H, m, V/H-6), 5.53 (0.5H, s, OH), 5.55 (0.4H, m, Y/H-6), 6.02 (0.1H, m, U/H-6), 6.04 (0.2H, m, W/H-6), 6.70-7.60 (16H, m, Ar), 8.40-8.60 (2H, m, αPyr).

Aufarbeitung

  1. customPurification by flash chromatography (hexane/ethyl acetate 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-204ad2f8daa54cdabc97edd3d45c12ea
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09198420B2

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