Diisopropylethylamine → HCID 89573439, Verbindung

HRID 2282909Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2282909
[CH3:1][N:2]1[CH2:40][CH2:39][CH2:38][C@@:3]1([CH3:41])[C:4]([NH:6][C@H:7]([C:11]([N:13]([C@@H:15]([C@@H:34]([CH3:37])[CH2:35][CH3:36])[C@H:16]([O:32][CH3:33])[CH2:17][C:18](=[O:31])OC1C(F)=C(F)C(F)=C(F)C=1F)[CH3:14])=[O:12])[CH:8]([CH3:10])[CH3:9])=[O:5].C(N(C(C)C)CC)(C)C.Cl.[CH3:52][O:53][C@@H:54]([C@@H:60]1[CH2:64][CH2:63][CH2:62][NH:61]1)[C@@H:55]([CH3:59])[C:56]([OH:58])=[O:57]>ClCCl>[CH3:1][N:2]1[CH2:40][CH2:39][CH2:38][C@@:3]1([CH3:41])[C:4]([NH:6][C@H:7]([C:11]([N:13]([C@@H:15]([C@@H:34]([CH3:37])[CH2:35][CH3:36])[C@H:16]([O:32][CH3:33])[CH2:17][C:18]([N:61]1[CH2:62][CH2:63][CH2:64][C@H:60]1[C@H:54]([O:53][CH3:52])[C@H:55]([C:56]([OH:58])=[O:57])[CH3:59])=[O:31])[CH3:14])=[O:12])[CH:8]([CH3:9])[CH3:10])=[O:5]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 69019103HCID 69019103, VerbindungHCID 866857681,2-dimethyl-L-prolyl-N-[(3R,4S,5S)-3-methoxy-5-methyl-1-oxo-1-(pentafluorophenoxy)heptan-4-yl]-N-methyl-L-valinamide

Produkt 1

HCID 89573439HCID 89573439, VerbindungAusbeute 34,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a cooled solution (0° C.) of #204 (8.0 g, 10.77 mmol, 1 eq.) in dichloromethane (25 mL) was added dropwise diisopropylethylamine (5.6 g, 43.08 mmol, 4 eq.) followed by a solution of #103 (3.22 g, 10.77 mmol, 1 eq.) in dichloromethane (15 mL). After the addition, the mixture was stirred at room temperature for 16 hours and the solvent was removed in vacuo. The residue was purified by silica gel chromatography (Gradient: 1 to 10% methanol in dichloromethane) to give #205 (2.2 g, 33%) as a yellow solid HPLC (Protocol X): m/z 597.42 [M+H+], retention time=8.729 minutes (purity >97%), Chiral HPLC retention time: 2.87 min (purity=89%) Column: Chiralcel OD-3, 150×4.6 mm, 3 μm; Mobile phase: ethanol (0.05% diethylamine) in CO2 from 5% to 40% over 12 minutes; Flow rate: 2.5 mL/minute.

Aufarbeitung

  1. additionAfter the addition
  2. customthe solvent was removed in vacuo
  3. customThe residue was purified by silica gel chromatography (Gradient: 1 to 10% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-45bb19fd0fb14030a50758f56bf56d4f
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09138486B2

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