Cesium carbonate → HCID 57968585, Verbindung

HRID 882758Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 882758
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[C:14]([N:16]1[CH2:22][CH2:21][CH2:20][N:19]([CH:23]2[CH2:26][CH2:25][CH2:24]2)[CH2:18][CH2:17]1)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].I[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.CC1C=NC2C(C=1C)=CC=C1C=2N=CC(C)=C1C.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.[Cu]I>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:10][C@H:9]1[C:14]([N:16]1[CH2:22][CH2:21][CH2:20][N:19]([CH:23]2[CH2:24][CH2:25][CH2:26]2)[CH2:18][CH2:17]1)=[O:15])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 11575IodobenzeneHCID 742653,4,7,8-Tetramethyl-1,10-phenanthrolineHCID 44600522HCID 44600522, Verbindung

Produkt 1

HCID 57968585HCID 57968585, VerbindungAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a stirred suspension of (2S,4R)-2-(4-cyclobutyl-[1,4]diazepane-1-carbonyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (116 mg, 0.32 mmol) in toluene (0.65 ml) was added iodobenzene (129 mg, 0.63 mmol), copper (I) iodide (6 mg, 0.032 mmol), 3,4,7,8-tetramethyl-1,10-phenanthroline (15 mg, 0.063 mmol), and Cs2CO3 (206 mg, 0.63 mmol). The resulting suspension was heated at 100° C. in a capped scintillation vial with stirring for 2 days. The reaction mixture was filtered through diatomaceous earth, washing with CH2Cl2. The filtrate was dried and concentrated. Purification of the residue by FCC provided the desired product (97.7 mg, 70%). MS (ESI): mass calcd. for C25H37N3O4, 443.3; m/z found, 444.3 [M+H]+. 1H NMR (CDCl3): 7.30-7.25 (m, 2H), 6.96 (dd, J=14.5, 7.2 Hz, 1H), 6.85 (dd, J=7.7, 5.5 Hz, 1H), 5.04-4.91 (m, 1H), 4.88-4.71 (m, 1H), 3.89-3.43 (m, 6H), 2.92-2.79 (m, 1H), 2.70-2.20 (m, 6H), 2.07-1.74 (m, 7H), 1.71-1.52 (m, 2H), 1.43-1.41 (m, 9H).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. washwashing with CH2Cl2
  3. customThe filtrate was dried
  4. concentrationconcentrated
  5. customPurification of the residue by FCC

Quellen und Nachweise

ORD-Eintrag
ord-eefb40f298aa4e079c590b6fb5d015d9
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236792B2

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