Water → HCID 15616710, Verbindung

HRID 1383222

Reaktionsgleichung

Reaktionsgleichung von HRID 1383222
[CH3:1][CH:2]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[NH:5]1)[CH3:3].C([Li])CCC.[CH:15]1([CH:18]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[C:19](Cl)=[O:20])[CH2:17][CH2:16]1.O>O1CCCC1>[Cl:28][C:25]1[CH:24]=[CH:23][C:22]([CH:18]([CH:15]2[CH2:17][CH2:16]2)[C:19]([N:5]2[C@@H:4]([CH:2]([CH3:3])[CH3:1])[CH2:8][O:7][C:6]2=[O:9])=[O:20])=[CH:27][CH:26]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7157133(4S)-4-(propan-2-yl)-1,3-oxazolidin-2-oneHCID 15083505alpha-Cyclopropyl-4-chlorophenylacetyl chlorideHCID 178418339Butyllithium

Produkt 1

HCID 15616710HCID 15616710, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

In a separate reaction vessel a stirred solution of 2.0 grams (0.016 mole) of (S)-4-(1-methylethyl)-2-oxazolidinone in 50 mL of tetrahydrofuran was cooled to -78° C., and 6.25 mL (0.016 mole) of n-butyllithium (2.5 molar in hexane) was added dropwise. Upon completion of addition, the reaction mixture was stirred for 30 minutes, and then the 2-cyclopropyl-2-(4-chlorophenyl)acetyl chloride, prepared above, was added dropwise during several minutes. Upon completion of addition, the reaction mixture was stirred for an additional 30 minutes and then was poured into water. The organic layer was separated and washed with one portion of aqueous sodium bicarbonate. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residual oil. The oil was subjected to chromatography on silica gel using hexane:diethyl ether (3:1) as eluant. The appropriate fractions were combined and concentrated under reduced pressure, yielding 0.85 gram of diastereomer (A) and 0.8 gram of diastereomer (B) of (S)-N-[2-(4-chlorophenyl)-2-cyclopropylacetyl]-4-(1-methylethyl)-2-oxazolidinone. Upon standing, diastereomer (A) crystallized to a solid, m.p. 61°-64° C.

Aufarbeitung

  1. additionUpon completion of addition
  2. additionwas added dropwise during several minutes
  3. additionUpon completion of addition
  4. stirringthe reaction mixture was stirred for an additional 30 minutes
  5. customThe organic layer was separated
  6. washwashed with one portion of aqueous sodium bicarbonate
  7. dry with materialThe organic layer was dried with magnesium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure to a residual oil
  10. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a711fc8fb4b34bcca3fdac245377932c
Quelldatensatz
uspto-grants-1989_02
Patentnummer
US04808762

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