Triethylamine → N-[2'-(4''-Acetamidocinnamoyloxy)ethyl]-5-(alpha-hydroxy-alpha-2-pyridylbenzyl)-7-(alpha-2-pyridyl benzylidene)-5-norbornene-2,3-dicarboximide

HRID 1496799Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1496799
[OH:1][C:2]([C:15]1[CH:16]2[C:21](=[C:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:19]([CH:20]=1)[CH:18]1[C:35]([N:37]([CH2:40][CH2:41]OC(=O)C=CC3C=CC(C(C)C)=CC=3)[C:38](=[O:39])[CH:17]21)=[O:36])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:56]([NH:59][C:60]1[CH:70]=[CH:69][C:63]([CH:64]=[CH:65][C:66]([OH:68])=[O:67])=[CH:62][CH:61]=1)(=[O:58])[CH3:57].C(N=C=NCCCN(C)C)C.C(N(CC)CC)C.CN(C1C=CC=CN=1)C>ClCCl>[C:56]([NH:59][C:60]1[CH:70]=[CH:69][C:63]([CH:64]=[CH:65][C:66]([O:68][CH2:41][CH2:40][N:37]2[C:38](=[O:39])[CH:17]3[CH:18]([CH:19]4[C:21](=[C:22]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=5)[C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=5)[CH:16]3[C:15]([C:2]([OH:1])([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=3)[C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)=[CH:20]4)[C:35]2=[O:36])=[O:67])=[CH:62][CH:61]=1)(=[O:58])[CH3:57]

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 218852-DimethylaminopyridineHCID 2515224-Acetylaminocinnamic acidHCID 1178180985-(alpha-Hydroxy-alpha-2-pyridylbenzyl)-N-[2'-(4''-isopropylcinnamoyloxy)ethyl]-7-(alpha-2-pyridyl benzylidene)-5-norbornene-2,3-dicarboximide

Produkt 1

HCID 117818190N-[2'-(4''-Acetamidocinnamoyloxy)ethyl]-5-(alpha-hydroxy-alpha-2-pyridylbenzyl)-7-(alpha-2-pyridyl benzylidene)-5-norbornene-2,3-dicarboximideAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A similar procedure (Schwartz, E. et al. Macromolecules 2011, 44, 4735-4741) to that previously described for the preparation of 347 was followed using 2 (1.50 g, 2.70 mmol), 4-acetamidocinnamic acid (0.50 g, 2.46 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (1.04 g, 5.60 mmol), triethylamine (1.24 mL, 8.91 mmol) and dimethylaminopyridine (60 mg, 0.49 mmol) in dichloromethane (25 mL), at room temperature for 72 h. Purification by flash chromatography (hexane/ethyl acetate 1:4) afforded 337 as a white solid (2.0 g, 2.69 mmol, 99%). mp 125-130° C.; 1H NMR (300 MHz, CDCl3) δ 2.17 (3H, s, NHAc), 3.35-3.90 (4.16H, m, NCH2CH2O, H-2, H-3, W/H-4), 3.83-3.95 (0.84H, m, U/H-1, V/H-1, Y/H-4), 4.14 (0.14H, m, U/H-4), 4.28-4.38 (2.32H, m, NCH2CH2O, V/H-4), 4.43-4.47 (0.54H, m, W/H-1, Y/H-1), 5.53 (0.32H, dd, J=3.4 and 1.2 Hz, V/H-6), 5.55 (0.38H, dd, J=3.4 and 1.2 Hz, Y/H-6), 5.59 (s, OH), 5.60 (s, OH), 5.63 (s, OH), 5.69 (s, OH), 6.06 (0.14H, dd, J=3.4 and 1.2 Hz, U/H-6), 6.06 (0.16H, dd, J=3.4 and 1.2 Hz, W/H-6), 6.17 (0.30H, d, J=15.8 Hz, COCH═CH), 6.26 (0.70H, d, J=15.8 Hz, COCH═CH), 6.74-7.61 (21H, m, Ar and COCH═CH), 8.40-8.63 (2H, m, αPyr); m/z (ESI, 70 eV) 765 (MNa+, 100%); (Found MNa+ 765.2684, C46H38N4NaO6 requires 765.2687).

Aufarbeitung

  1. customPurification by flash chromatography (hexane/ethyl acetate 1:4)

Quellen und Nachweise

ORD-Eintrag
ord-c5c0c240d7984bc9ba23c5777f8f08c7
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09198420B2

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