Ethanaminium, N,N,N-triethyl-, fluoride (1:1) → HCID 16752763, Verbindung

HRID 253605

Reaktionsgleichung

Reaktionsgleichung von HRID 253605
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([C@@H:17]2[O:22][CH2:21][CH2:20][N:19]([C:23](=[O:47])[NH:24][C@H:25]([C@H:33]([OH:46])[CH2:34][N:35](C)[C:36](OCC[Si](C)(C)C)=O)[CH2:26][CH:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[CH2:18]2)[O:9][CH2:10][CH2:11][NH:12][C:13](=[O:16])[O:14][CH3:15])[CH:5]=[CH:6][CH:7]=1.[N+](CC)(CC)(CC)CC.[F-]>CC#N>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([C@@H:17]2[O:22][CH2:21][CH2:20][N:19]([C:23](=[O:47])[NH:24][C@H:25]([C@H:33]([OH:46])[CH2:34][NH:35][CH3:36])[CH2:26][CH:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[CH2:18]2)[O:9][CH2:10][CH2:11][NH:12][C:13](=[O:16])[O:14][CH3:15])[CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 69582Ethanaminium, N,N,N-triethyl-, fluoride (1:1)HCID 66861750HCID 66861750, Verbindung

Produkt 1

HCID 16752763HCID 16752763, VerbindungAusbeute 12,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A 10 mL flask was charged with methyl 2-((S)-(3-chlorophenyl)((R)-4-((2S,3R)-3-hydroxy-4-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)-1-(tetrahydro-2H-pyran-4-yl)butan-2-ylcarbamoyl)morpholin-2-yl)methoxy)ethylcarbamate (30 mg, 0.043 mmol) dissolved in MeCN (4 mL) and Et4NF (14 mg, 0.094 mmol) was added. The mixture was stirred for 0.5 h under reflux. After stirring, it was monitored by HPLC until the reaction ended. The solution was concentrated in vacuo and purified by HPLC to give the target compound (2.97 mg, 12%). 1H NMR (MeOD) 1.27-1.30 (m, 2H), 1.32-1.40 (m, 2H), 1.51-1.62 (m, 2H), 1.65-1.80 (m, 2H), 2.70 (s, 3H), 1.75-1.90 (m, 2H), 1.90-3.10 (m, 4H), 3.65 (s, 3H), 3.80-3.95 (m, 5H), 4.05-4.20 (m, 1H), 4.30 (m, 1H), 7.25-7.40 (m, 4H).

Aufarbeitung

  1. temperatureunder reflux
  2. stirringAfter stirring
  3. concentrationThe solution was concentrated in vacuo
  4. custompurified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-30caf40a8ac34126bfc62f556e4938bb
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872028B2

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