Ethyl Acetate → HCID 54708345, Verbindung

HRID 348114

Reaktionsgleichung

Reaktionsgleichung von HRID 348114
C(O[C:4](=[O:22])[CH2:5][C:6]1([C:17]([O:19][CH2:20][CH3:21])=[O:18])O[N:13]2[C:8]([C:9]([CH3:16])([CH3:15])[O:10][CH2:11][CH2:12]2)=[N:7]1)C.C(OCC)(=[O:25])C>CC1C=CC(C)=CC=1C.CCOCC>[OH:25][C:5]1[C:4](=[O:22])[N:13]2[C:8]([C:9]([CH3:15])([CH3:16])[O:10][CH2:11][CH2:12]2)=[N:7][C:6]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Komponenten

5

Edukt 2

HCID 8857Ethyl AcetateHCID 21069948HCID 21069948, Verbindung

Produkt 1

HCID 54708345HCID 54708345, VerbindungAusbeute 18 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 72471,2,4-TrimethylbenzeneLösungsmittel

Versuchsvorschrift

A solution of intermediate 24, ethyl 2-(2-ethoxy-2-oxoethyl)-8,8-dimethyl-2,5,6,8-tetrahydro-[1,2,4]oxadiazolo[3,2-c][1,4]oxazine-2-carboxylate (31.16 g) in 1,2,4-trimethylbenzene (200 mL) was heated at 180° C. for 5 h. The resulting dark reaction solution was cooled then concentrated to give a dark brown paste which was taken up into ethyl acetate (250 mL) and extracted with 0.5 M aq Na2CO3 (4×50 mL). The organic layer was discarded and the aqueous layer acidified by carefully adding conc. HCl (20 mL) before being extracted with CH2Cl2 (4×50 mL). The combined CH2Cl2 layers were dried (Na2SO4), filtered and concentrated to give a dark paste which was dissolved in ether (100 mL) and allowed to stand at room temperature in a open flask. The brown/light yellow solid that formed was filtered to afford the title compound. The mother liquor that contained product was re-processed to afford additional material (combined yield ˜18–20% over two steps). 1H NMR (500 MHz, CDCl3) δ: 10.55 (1H, s), 4.45 (2H, q, J=7.0 Hz), 4.02 (4H, s), 1.61 (6H, s), 1.43 (3H, t, J=7.0 Hz). HRMS (M+H) calcd for C12H17N2O5: 269.1138; found: 269.1149. Anal calcd for C12H16N2O5: C, 53.72; H, 6.01; N, 10.44. Found: C, 53.71; H, 6.04; N, 10.30.

Aufarbeitung

  1. temperatureThe resulting dark reaction solution was cooled
  2. concentrationthen concentrated
  3. customto give a dark brown paste which
  4. extractionextracted with 0.5 M aq Na2CO3 (4×50 mL)
  5. extractionbefore being extracted with CH2Cl2 (4×50 mL)
  6. dry with materialThe combined CH2Cl2 layers were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a dark paste which
  10. customto stand at room temperature in a open flask
  11. customThe brown/light yellow solid that formed
  12. filtrationwas filtered

Quellen und Nachweise

ORD-Eintrag
ord-5444f08f79884fccbaa0895d41347e5d
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176196B2

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