Triethylamine → N-(2-Chloro-6-fluorobenzyl)-3-{3-[(2R)-2-({(2R)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)propyl]phenyl}propanamide

HRID 916064

Reaktionsgleichung

Reaktionsgleichung von HRID 916064
[OH:1][C@H:2]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([CH2:26][OH:27])[CH:20]=1)[CH2:3][NH:4][C@H:5]([CH3:18])[CH2:6][C:7]1[CH:8]=[C:9]([CH2:13][CH2:14][C:15](O)=[O:16])[CH:10]=[CH:11][CH:12]=1.[F:28][C:29]1[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[C:30]=1[CH2:31][NH2:32].C(N(CC)CC)C>CN(C)C=O>[NH3:4].[Cl:37][C:33]1[CH:34]=[CH:35][CH:36]=[C:29]([F:28])[C:30]=1[CH2:31][NH:32][C:15](=[O:16])[CH2:14][CH2:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([CH2:6][C@H:5]([NH:4][CH2:3][C@H:2]([OH:1])[C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([CH2:26][OH:27])[CH:20]=2)[CH3:18])[CH:8]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 848332-Chloro-6-fluorobenzylamineHCID 589598143-{3-[(2R)-2-({(2R)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)propyl]phenyl}propanoic acid

Produkt 2

HCID 222AmmoniaHCID 11226068N-(2-Chloro-6-fluorobenzyl)-3-{3-[(2R)-2-({(2R)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)propyl]phenyl}propanamideAusbeute 40,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 3-{3-[(2R)-2-({(2R)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)propyl]phenyl}propanoic acid (Preparation 60) (150 mg, 0.29 mmol), O-(1H-benzotrizol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (133 mg, 0.35 mmol), 2-fluoro-6-chlorobenzylamine (56 mg, 0.35 mmol) and triethylamine (0.12 ml, 0.88 mmol) were stirred at room temperature for 16 hours in N,N-dimethylformamide (3 ml). The solvent was removed in vacuo and the resulting brown oil was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (98:2:0.2 followed by 94:6:0.6 by volume) to give the title compound as a white foam (30 mg).

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. customthe resulting brown oil was purified by flash column chromatography on silica gel eluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-5e9630c9cf1e43349515ed3c6211291d
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07268147B2

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