Potassium Carbonate → [4-(4-{4-[2-(4-Benzyloxy-3-formylaminophenyl)-2-(R)-hydroxyethylamino]pentyl}-phenyl)butyl]carbamic acid benzyl ester

HRID 1696836Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1696836
[CH2:1]([O:8][C:9](=[O:27])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH:24]([NH2:26])[CH3:25])=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:28]([O:35][C:36]1[CH:41]=[CH:40][C:39]([C@@H:42]([OH:45])[CH2:43]Br)=[CH:38][C:37]=1[NH:46][CH:47]=[O:48])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9](=[O:27])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH:24]([NH:26][CH2:43][C@@H:42]([C:39]2[CH:40]=[CH:41][C:36]([O:35][CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[C:37]([NH:46][CH:47]=[O:48])[CH:38]=2)[OH:45])[CH3:25])=[CH:17][CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 11142645(R)-N-[5-(2-Bromo-1-hydroxyethyl)-2-(phenylmethoxy)phenyl]formamideHCID 58100158{4-[4-(4-Aminopentyl)phenyl]butyl}carbamic acid benzyl ester

Produkt 1

HCID 86649686[4-(4-{4-[2-(4-Benzyloxy-3-formylaminophenyl)-2-(R)-hydroxyethylamino]pentyl}-phenyl)butyl]carbamic acid benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A suspension composed of compound 26 (0.59 g, 1.60 mmol), compound 5 (0.42 g, 1.19 mmol); K2CO3 (0.23 g, 1.68 mmol) and chloroform (25 mL) was heated to reflux for 72 h, then cooled to ambient temperature. The solid was vacuum filtered and washed with chloroform (3×10 mL). The filtrate and the washings were combined and concentrated. The residue was subjected to column chromatography eluting with 0-10% methanol in dichloromethane. The un-reacted starting material 26 (0.39 g; 66% recovery) was recovered in the separation. A mixture of two diastereomers of the desired products 27, which were not separable in this step, was obtained (0.29 g, 28%) as a colorless, viscous oil: 1H NMR (500 MHz, CDCl3) δ 1.08 (d, 3H), 1.37 (m, 2H), 1.48-1.68 (m, 6H), 2.55 (m, 4H), 2.74 (br, 2H), 2.92 (m, 1H), 3.18 (m, 2H), 3.58 (m, 1H), 3.72 (m, 1H), 4.70 (m, 1H), 4.80 (br, 1H), 5.08 (m, 4H), 6.92 (m, 1H), 7.08 (m, 5H), 7.22 (t, 1H), 7.34 (m, 10H), 7.92 (s, 1H), 8.31 (s, 1H); m/z (ESI) 638 [C39H47N3O5+H]+.

Aufarbeitung

  1. temperatureto reflux for 72 h
  2. filtrationfiltered
  3. washwashed with chloroform (3×10 mL)
  4. concentrationconcentrated
  5. washeluting with 0-10% methanol in dichloromethane
  6. customwas recovered in the separation
  7. additionA mixture of two diastereomers of the desired products 27, which
  8. customwas obtained (0.29 g, 28%) as a colorless, viscous oil

Quellen und Nachweise

ORD-Eintrag
ord-01a5b76369b14de5a7354e365f319a1a
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163758B2

Notizen zur Reaktion

Wird geladen…