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Toluene → Tert-butyl 3-cyclohexylmethyl-4-(4-isopropyl-2-oxooxazolidin-3-yl)-4-oxobutyrate

HRID 1060743
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1060743
C[Si](C)(C)[N-][Si](C)(C)C.[Na+].C1(C)C=CC=CC=1.[CH:18]1([CH2:24][CH2:25][C:26]([N:28]2[C@@H:32]([CH:33]([CH3:35])[CH3:34])[CH2:31][O:30][C:29]2=[O:36])=[O:27])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[C:37]([O:41][C:42](=[O:45])[CH2:43]Br)([CH3:40])([CH3:39])[CH3:38]>C1COCC1.Cl>[CH:18]1([CH2:24][CH:25]([C:26]([N:28]2[CH:32]([CH:33]([CH3:34])[CH3:35])[CH2:31][O:30][C:29]2=[O:36])=[O:27])[CH2:43][C:42]([O:41][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:45])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 79177tert-Butyl bromoacetateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 69156991(S)-3-cyclohexylpropionyl-4-isopropyloxazolidin-2-one

Produkt 1

HCID 18628724Tert-butyl 3-cyclohexylmethyl-4-(4-isopropyl-2-oxooxazolidin-3-yl)-4-oxobutyrateAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 313Hydrochloric AcidLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

A solution of sodium hexamethyldisilazide (92.4 mL of a 0.6M toluene solution, Aldrich) in THF (70 mL) was cooled to −78° C. and then treated with a solution of (S)-3-cyclohexylpropionyl-4-isopropyloxazolidin-2-one (10.5 g, 39.3 mmol) in THF (30 mL) added dropwise over 10 minutes. The mixture was stirred for 1 hour and then treated with a solution of tert-butylbromoacetate (9.75 mL, 50 mmol) in THF (20 mL) added dropwise. The mixture was stirred for 1 hour, while warming to −10° C. The mixture reaction was diluted with 1M hydrochloric acid (100 mL) and the dilution was extracted with ethyl acetate (200 mL). The extract was washed with saturated aqueous sodium bicarbonate (100 mL) and brine (100 mL), dried (MgSO4), filtered and concentrated to dryness. The residue was dissolved in hexane and product was crystallized out to provide tert-butyl 3-cyclohexylmethyl-4-(4-isopropyl-2-oxooxazolidin-3-yl)-4-oxobutyrate (9.09 g, 61%). MS (M+1): 382.

Aufarbeitung

  1. additionadded dropwise over 10 minutes
  2. additionadded dropwise
  3. stirringThe mixture was stirred for 1 hour
  4. customThe mixture reaction
  5. extractionthe dilution was extracted with ethyl acetate (200 mL)
  6. washThe extract was washed with saturated aqueous sodium bicarbonate (100 mL) and brine (100 mL)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated to dryness
  10. dissolutionThe residue was dissolved in hexane
  11. customproduct was crystallized out

Quellen und Nachweise

ORD-Eintrag
ord-09da4d66629e49eabacfb64ab6fe6c0a
Quelldatensatz
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06525036B2

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