Water → Phenyl 1,1-bis(phenylmethyl)-tetrahydro-3-oxo-3H-oxazolo[3,4-a]pyrazine-7(1H)-carboxylate

HRID 1713543Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1713543
[C:1]1([CH2:7][C:8]2([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:12]3[CH2:13][NH:14][CH2:15][CH2:16][N:11]3[C:10](=[O:17])[O:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:32](Cl)(=[O:40])[O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.O>O1CCCC1>[C:19]1([CH2:18][C:8]2([CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:12]3[CH2:13][N:14]([C:32]([O:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[O:40])[CH2:15][CH2:16][N:11]3[C:10](=[O:17])[O:9]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 231219731,1-Bis(phenylmethyl)-hexahydro-3H-oxazolo[3,4-a]pyrazin-3-one

Produkt 1

HCID 23121845Phenyl 1,1-bis(phenylmethyl)-tetrahydro-3-oxo-3H-oxazolo[3,4-a]pyrazine-7(1H)-carboxylateAusbeute 85,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1,1-bis(phenylmethyl)-hexahydro-3H-oxazolo[3,4-a]pyrazin-3-one (0.16 g, 0.50 mmol) in tetrahydrofuran (10 mL) were sequentially added triethylamine (0.14 mL) and phenyl chlorocarbonate (0.12 g, 0.75 mmol), and the mixture was stirred at room temperature for 3 hours. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The extract was washed with a 0.5 M aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=10:1 to ethyl acetate). The fractions were concentrated, and to the obtained crystals was added diisopropyl ether, collected by filtration and washed with diisopropyl ether to obtain the title compound (0.19 g, yield 85%).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with a 0.5 M aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=10:1 to ethyl acetate)
  6. concentrationThe fractions were concentrated
  7. additionto the obtained crystals was added diisopropyl ether
  8. filtrationcollected by filtration
  9. washwashed with diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-663a86ed7d894d71b52be84eea1667fe
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795267B2

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