1,10-Phenanthroline → HCID 21071235, Verbindung

HRID 1372172Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1372172
C(OC(=O)[NH:10][CH:11]1[CH2:16][CH2:15][CH2:14][NH:13][C:12]1=[O:17])C1C=CC=CC=1.I[C:20]1[CH:25]=[CH:24][C:23]([C:26]2([C:29]([OH:31])=[O:30])[CH2:28][CH2:27]2)=[CH:22][CH:21]=1.[C:32]([O-:35])([O-])=[O:33].[K+].[K+].N1[C:51]2[C:42](=[CH:43][CH:44]=[C:45]3[C:50]=2N=CC=C3)[CH:41]=CC=1>CS(C)=O.[Cu]I.O.CCOC(C)=O>[CH2:41]([O:35][C:32]([C:11]1([NH2:10])[CH2:16][CH2:15][CH2:14][N:13]([C:20]2[CH:25]=[CH:24][C:23]([C:26]3([C:29]([OH:31])=[O:30])[CH2:28][CH2:27]3)=[CH:22][CH:21]=2)[C:12]1=[O:17])=[O:33])[C:42]1[CH:51]=[CH:50][CH:45]=[CH:44][CH:43]=1

Komponenten

9

Edukt 4

HCID 13181,10-PhenanthrolineHCID 11430Potassium CarbonateHCID 13556445Benzyl (2-oxopiperidin-3-yl)carbamateHCID 217064771-(4-Iodophenyl)cyclopropane-1-carboxylic acid

Produkt 1

HCID 21071235HCID 21071235, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Part A. To a mixture of (2-oxo-piperidin-3-yl)-carbamic acid benzyl ester (1.35 g, 5.44 mmol) and 1-(4-iodo-phenyl)-cyclopropanecarboxylic acid (1.56 g, 5.42 mmol, 1.0 eq) in DMSO (5 mL) was added K2CO3 (3.00 g, 21.73 mmol, 4.0 eq), CuI (0.52 g, 2.74 mmol, 0.5 eq), and 1,10-phenanthroline (0.50 g, 2.74 mmol, 0.5 eq) sequentially. The mixture was heated at 120° C. overnight under N2. After cooling, EtOAc and H2O was added. The mixture was filtered. The filtrate was washed with 1N NaOH. The aqueous layer was acidified with conc. HCl, and extracted with EtOAc (3×). The organics were washed with brine, dried over MgSO4, filtered, and concentrated to give crude 1-[4-(3-benzyloxycarbonyl-amino-2-oxo-piperidin-1-yl)-phenyl]-cyclopropanecarboxylic acid (0.69 g, slightly contaminated with disubstituted compound). LC/MS (ESI) 409.2 (M+H).

Aufarbeitung

  1. temperatureAfter cooling
  2. filtrationThe mixture was filtered
  3. washThe filtrate was washed with 1N NaOH
  4. extractionextracted with EtOAc (3×)
  5. washThe organics were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ca2910d92ab944c1b0f43c78076e8121
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157470B2

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