Sodium Carbonate → HCID 68520083, Verbindung

HRID 1515349

Reaktionsgleichung

Reaktionsgleichung von HRID 1515349
[NH2:1][CH:2]1[CH:9]2[CH2:10][C:5]3([C:12]([O:14][CH3:15])=[O:13])[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2.Cl[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18].[C:27](=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.O>[CH2:20]([O:19][C:17](=[O:18])[CH2:27][NH:1][CH:2]1[CH:9]2[CH2:10][C:5]3([C:12]([O:14][CH3:15])=[O:13])[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformate2×HCID 57425932Methyl 4-aminoadamantane-1-carboxylate

Produkt 1

HCID 68520083HCID 68520083, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of methyl 4-aminoadamantane-1-carboxylate obtained in Reference Example 11 (1.87 g) in tetrahydrofuran (20 ml), water (10 ml), benzyl chloroformate (1.53 g) and sodium carbonate (1.13 g) were added and stirred at room temperature for 5 hours. Benzyl chloroformate (0.76 g) was further added and stirred at room temperature for 2 hours. After insoluble materials were filtered off, the solvent was concentrated and the residue was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and then filtered to remove the desiccant, followed by distilling off the solvent under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluting solvent: chloroform:methanol=200:1 to 100:1) to give methyl 4-{[2-(benzyloxy)-2-oxoethyl]amino}-adamantane-1-carboxylate (3.30 g) as a colorless powder.

Aufarbeitung

  1. additionwere added
  2. stirringstirred at room temperature for 2 hours
  3. filtrationAfter insoluble materials were filtered off
  4. concentrationthe solvent was concentrated
  5. extractionthe residue was extracted with chloroform
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customto remove the desiccant
  9. distillationby distilling off the solvent under reduced pressure
  10. customThe resulting residue was purified by silica gel column chromatography (eluting solvent: chloroform:methanol=200:1 to 100:1)

Quellen und Nachweise

ORD-Eintrag
ord-8912306657ff4f32a49c1ff8bdc8eddc
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222417B2

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