Acetic Anhydride → (R)-{1-[8-Acetyl-3-(4-ethoxy-phenyl)-4-oxo-3,4,5,6,7,8-hexahydro-pyrido[2,3-d]pyrimidin-2-yl]-ethyl}-carbamic acid tert-butyl ester

HRID 2223145Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2223145
[C:1]([O:5][C:6](=[O:30])[NH:7][CH:8]([C:10]1[N:11]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH3:29])=[CH:23][CH:22]=2)[C:12](=[O:20])[C:13]2[CH2:19][CH2:18][CH2:17][NH:16][C:14]=2[N:15]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.[C:40](OC(=O)C)(=[O:42])[CH3:41]>>[C:1]([O:5][C:6](=[O:30])[NH:7][C@@H:8]([C:10]1[N:11]([C:21]2[CH:22]=[CH:23][C:24]([O:27][CH2:28][CH3:29])=[CH:25][CH:26]=2)[C:12](=[O:20])[C:13]2[CH2:19][CH2:18][CH2:17][N:16]([C:40](=[O:42])[CH3:41])[C:14]=2[N:15]=1)[CH3:9])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 69201576{1-[3-(4-Ethoxy-phenyl)-4-oxo-3,4,5,6,7,8-hexahydro-pyrido[2,3-d]pyrimidin-2-yl]-ethyl}-carbamic acid tert-butyl ester

Produkt 1

HCID 58617397(R)-{1-[8-Acetyl-3-(4-ethoxy-phenyl)-4-oxo-3,4,5,6,7,8-hexahydro-pyrido[2,3-d]pyrimidin-2-yl]-ethyl}-carbamic acid tert-butyl ester

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

D2 (263 mg, 0.63 mmol) and N,N-diisopropylethylamine (111 μL, 0.63 mmol) were dissolved in acetic anhydride (10 mL) and heated to 80° C. The reaction stirred overnight. It was quenched with saturated aqueous sodium bicarbonate, then extracted with dichloromethane. The organic layer was washed with saturated aqueous sodium bicarbonate and brine, then dried over magnesium sulfate, filtered, concentrated in vacuo. Purified by chromatography (1:1 to 1:2 hexane:ethyl acetate), recovering 168 mg of D3.

Aufarbeitung

  1. customIt was quenched with saturated aqueous sodium bicarbonate
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurified by chromatography (1:1 to 1:2 hexane:ethyl acetate)
  8. customrecovering 168 mg of D3

Quellen und Nachweise

ORD-Eintrag
ord-1a61ea1a48d44e53921c65fe078abba8
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07375102B2

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