Water → 5-[3,3''-Dichloro-5'-(8-indol-1-yl-octylcarbamoyl)-[1,1';3',1'']terphenyl-2'-yloxy]-pentanoic acid, ethyl ester

HRID 1281427

Reaktionsgleichung

Reaktionsgleichung von HRID 1281427
[N:1]1([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19](=[O:41])[C:20]2[CH:25]=[C:24]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=3)[C:23]([OH:33])=[C:22]([C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[CH:35]=3)[CH:21]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C([O-])([O-])=O.[K+].[K+].[CH2:48]([O:50][C:51](=[O:57])[CH2:52][CH2:53][CH2:54][CH2:55]Br)[CH3:49].O>CN(C=O)C>[Cl:32][C:28]1[CH:27]=[C:26]([C:24]2[CH:25]=[C:20]([C:19](=[O:41])[NH:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][N:1]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH:3]=[CH:2]3)[CH:21]=[C:22]([C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[CH:35]=3)[C:23]=2[O:33][CH2:55][CH2:54][CH2:53][CH2:52][C:51]([O:50][CH2:48][CH3:49])=[O:57])[CH:31]=[CH:30][CH:29]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 84580Ethyl 5-bromovalerateHCID 22237625N-(8-indol-1-yl-octyl)-3,5-bis(3-chlorophenyl)4-hydroxybenzamide

Produkt 1

HCID 865836655-[3,3''-Dichloro-5'-(8-indol-1-yl-octylcarbamoyl)-[1,1';3',1'']terphenyl-2'-yloxy]-pentanoic acid, ethyl esterAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of N-(8-indol-1-yl-octyl)-3,5-bis(3-chlorophenyl)-4-hydroxybenzamide (0.399 g, 0.68 mmol), K2CO3 (0.116 g, 0.84 mmol), and ethyl-5-bromovalerate (0.176 g, 0.84 mmol) in DMF was stirred at room temperature under nitrogen. After ˜48 h, the reaction mixture was poured into water (40 ml) and extracted with EtOAc (1×20 ml, 4×10 ml). The combined extracts were washed with water (3×10 ml), brine (2×10 ml), dried over Na2SO4, filtered and the filtrate concentrated in vac and dried. The crude product was purified by flash chromatography (alumina, hexane, 10% and 60% EtOAc/Hex) to give the desired product as a light yellow oil (0.432 g, 86%); (400 MHz, DMSO-d6) δ 1.12-1.30 (m, 15H), 1.44-1.55 (m, 2H), 1.67-1.76 (m, 2H), 1.92 (t, J=7 Hz, 2H), 3.16-3.27 (m, 4H), 3.98 (q, J=7 Hz, 2H), 4.12 (t, J=7.2 Hz, 2H), 6.38 (d, J=3.1 Hz, 1H), 6.95-6.99 (m, 1H), 7.06-7.10 (m, 1H), 7.32 (d, J=3.3 Hz, 1H), 7.40-7.52 (m, 6H), 7.56-7.59 (m, 2H), 7.68 (t, J=1.8 Hz, 2H), 7.87 (s, 2H), 8.53 (t, J=5.7 Hz, 1H); IR (film) 3320, 2940, 2950, 1730, 1630, 1540, cm−1; mass spectrum [(+)APCI], m/z 713 (M+H)+.

Aufarbeitung

  1. extractionextracted with EtOAc (1×20 ml, 4×10 ml)
  2. washThe combined extracts were washed with water (3×10 ml), brine (2×10 ml)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated in vac
  6. customdried
  7. customThe crude product was purified by flash chromatography (alumina, hexane, 10% and 60% EtOAc/Hex)

Quellen und Nachweise

ORD-Eintrag
ord-bd8a564be26b4157af7171e383eff1c8
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06451827B2

Verknüpfte Notizen

Wird geladen…