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(2R)-Oxiran-2-ylmethyl butanoate → [3-[3,5-Difluoro-4-[4-(tert-butoxycarbonyl)-1-piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methanol

HRID 266710
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 266710
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([F:20])=[CH:18][C:17]([NH:21][C:22](OCC3C=CC=CC=3)=O)=[CH:16][C:15]=2[F:32])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)=O.CC(C)=O.[Li]CCCC.[CH2:45]([O:49][C:50](=[O:54])CCC)[C@@H:46]1[O:48]C1>C1COCC1.C(Cl)Cl.CO.C(Cl)(Cl)Cl>[F:20][C:19]1[CH:18]=[C:17]([N:21]2[CH2:22][CH:45]([CH2:46][OH:48])[O:49][C:50]2=[O:54])[CH:16]=[C:15]([F:32])[C:14]=1[N:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 2724536(2R)-Oxiran-2-ylmethyl butanoateHCID 18522661Acetone cardiceHCID 214626171-(Tert-butoxycarbonyl)-4-[2,6-difluoro-4-(benzyloxycarbonyl)aminophenyl]piperazineHCID 178418339Butyllithium

Produkt 1

HCID 21462612[3-[3,5-Difluoro-4-[4-(tert-butoxycarbonyl)-1-piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methanolAusbeute 86,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 21584188Chloroform methanolLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

The 1-(tert-butoxycarbonyl)-4-[2,6-difluoro-4-(benzyloxycarbonyl)aminophenyl]piperazine (14.05 g, 31 mmol) was dissolved in dry THF (150 mL) and then cooled to -78° C. (dry ice/acetone). The reaction was next treated with with n-BuLi (21.6 mL, 35 mmol) dropwise over a 25 minute period. The reaction was allowed to stir at -78° C. for 30 minutes and then (R)-(-)-glycidylbutyrate (4.89 mL, 35 mmol) was added dropwise over 7 minutes. The reaction was maintained at -78° C. for an additional 15 minutes and then the bath was removed, allowing the reaction to slowly warm up to room temperature overnight. The reaction was determined to be complete by TLC (5% MeOH/CHCl3, UV short wave). The reaction mixture was diluted with 500 mL CH2Cl2 and then washed with both H2O (3×300 mL) and brine (300 mL). The aqueous portions were back-extracted with more CH2Cl2 (3×400 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated to give a creamy yellow solid. The crude solid was purified by recrystallization from hot EtOAc/hexane to give 11.063 g (85%) of the title compound as a white solid with mp 164°-166° C.

Aufarbeitung

  1. temperatureThe reaction was maintained at -78° C. for an additional 15 minutes
  2. customthe bath was removed
  3. customthe reaction
  4. temperatureto slowly warm up to room temperature overnight
  5. washwashed with both H2O (3×300 mL) and brine (300 mL)
  6. extractionThe aqueous portions were back-extracted with more CH2Cl2 (3×400 mL)
  7. dry with materialThe combined organic extracts were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give a creamy yellow solid
  11. customThe crude solid was purified by recrystallization from hot EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-e202df859727451f9225014e2f35f7a8
Quelldatensatz
uspto-grants-1997_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05652238

Notizen zur Reaktion

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