1-Fluoro-4-(isocyanatomethyl)benzene → 1,1-Bis(phenylmethyl)-N-[(4-fluorophenyl)methyl]-tetrahydro-3-oxo-3H-oxazolo[3,4-a]pyrazine-7(1H)-carboxamide

HRID 1713542Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1713542
[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.[F:25][C:26]1[CH:35]=[CH:34][C:29]([CH2:30][N:31]=[C:32]=[O:33])=[CH:28][CH:27]=1>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]([NH:31][CH2:30][C:29]4[CH:34]=[CH:35][C:26]([F:25])=[CH:27][CH:28]=4)=[O:33])[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

4

Edukt 2

HCID 27333761-Fluoro-4-(isocyanatomethyl)benzeneHCID 231219731,1-Bis(phenylmethyl)-hexahydro-3H-oxazolo[3,4-a]pyrazin-3-one

Produkt 1

HCID 231220661,1-Bis(phenylmethyl)-N-[(4-fluorophenyl)methyl]-tetrahydro-3-oxo-3H-oxazolo[3,4-a]pyrazine-7(1H)-carboxamideAusbeute 71,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To 1,1-bis(phenylmethyl)-hexahydro-3H-oxazolo[3,4-a]pyrazin-3-one (0.16 g, 0.50 mmol) were added tetrahydrofuran (10 mL) and 4-fluorobenzyl isocyanate (0.30 g, 2.0 mmol), and the mixture was stirred at 50° C. for 4 hours. The reaction solution was concentrated, and then the residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1 to ethyl acetate). The fractions were collected and concentrated. To the residue was added diisopropyl ether, and the obtained solid matter was collected by filtration and washed with diisopropyl ether to obtain the title compound (0.17 g, yield 70%).

Aufarbeitung

  1. concentrationThe reaction solution was concentrated
  2. customthe residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1 to ethyl acetate)
  3. customThe fractions were collected
  4. concentrationconcentrated
  5. additionTo the residue was added diisopropyl ether
  6. filtrationthe obtained solid matter was collected by filtration
  7. washwashed with diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-679cbc83969347faa6aa6f893503fa16
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795267B2

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