Pyridine → HCID 136367326, Verbindung

HRID 227252Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 227252
[C:1]([O:5][C:6]([N:8]1[CH:12]([C:13]2[C:17]3[N:18]=[CH:19][NH:20][C:21](=[O:22])[C:16]=3[NH:15][CH:14]=2)[CH:11]([OH:23])[CH:10]([OH:24])[CH:9]1[CH2:25][OH:26])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:27](Cl)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[C:36]([O-:39])(O)=O.[Na+].C([O:44][CH2:45][CH3:46])(=O)C.N1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6]([N:8]1[CH:12]([C:13]2[C:17]3[N:18]=[CH:19][NH:20][C:21](=[O:22])[C:16]=3[NH:15][CH:14]=2)[CH:11]([O:23][C:27](=[O:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:10]([O:24][C:45](=[O:44])[C:46]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH:9]1[CH2:25][O:26][C:36](=[O:39])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 5

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 136367327HCID 136367327, Verbindung

Produkt 1

HCID 136367326HCID 136367326, VerbindungAusbeute 58,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 142844-(Dimethylamino)pyridineKatalysator

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

To a stirred solution of compound 1-2 from step 1 (5.85 g, 16.0 mmol) in pyridine (80 mL) is added benzoyl chloride (13.49 g, 96 mmol) and DMAP (0.05 g, 0.4 mmol) at RT. The reaction mixture is heated to 55° C. and then cooled to RT and stirred for 72 h. The reaction mixture is poured into saturated NaHCO3 (400 mL) and ethyl acetate (250 mL) and stirred for 1.5 h. The reaction mixture is extracted with ethyl acetate (2×1 L) and the combined organic extracts are washed with cold HCl (0.1 N, 400 mL), saturated NaHCO3 (1×200 mL), water (2×200 mL), and brine (1×250 mL) and dried (MgSO4). After filtration, the filtrate is concentrated and the crude residue is purified on silica gel column by flash chromatography using ethyl acetate in hexanes (0 to 100%) to afford 6.35 g (58.5%) of 3,4-bis-benzoyloxy-2-benzoyloxymethyl-5-(4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-7-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (1-3) as a gum.

Aufarbeitung

  1. temperaturecooled to RT
  2. stirringstirred for 1.5 h
  3. extractionThe reaction mixture is extracted with ethyl acetate (2×1 L)
  4. washthe combined organic extracts are washed with cold HCl (0.1 N, 400 mL), saturated NaHCO3 (1×200 mL), water (2×200 mL), and brine (1×250 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationAfter filtration
  7. concentrationthe filtrate is concentrated
  8. customthe crude residue is purified on silica gel column by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-82c0df05b03945f897b598094ffa1bb0
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560434B2

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