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Dichloromethane → (4R,5S)-4-Methyl-3-((R)-4-methyl-octanoyl)-5-phenyl-oxazolidin-2-one

HRID 28433
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 28433
[CH3:1][C@H:2]([CH2:8][CH2:9][CH2:10][CH3:11])[CH2:3][CH2:4][C:5]([OH:7])=O.[C:12](Cl)(=[O:16])[C:13](Cl)=O.[O:18]1[CH2:22][CH2:21][NH:20][C:19]1=O.[CH2:24]([Li])[CH2:25][CH2:26][CH3:27].[CH2:29](Cl)Cl>CN(C=O)C.C1COCC1>[CH3:22][C@@H:21]1[C@H:12]([C:13]2[CH:29]=[CH:24][CH:25]=[CH:26][CH:27]=2)[O:16][C:19](=[O:18])[N:20]1[C:5](=[O:7])[CH2:4][CH2:3][C@H:2]([CH3:1])[CH2:8][CH2:9][CH2:10][CH3:11]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 739492-OxazolidinoneHCID 6997333(4R)-4-methyloctanoic acidHCID 178418339Butyllithium

Produkt 1

HCID 57142278(4R,5S)-4-Methyl-3-((R)-4-methyl-octanoyl)-5-phenyl-oxazolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 6228DimethylformamideKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To (R)-4-methyl-octanoic acid (2.14 g, 13.5 mmol) in 25 mL CH2Cl2 at 0° C. was added 3 drops DMF, followed by oxalyl chloride (1.42 mL, 16.2 mmol) resulting in vigorous gas evolution. The solution was warmed directly to ambient temperature, stirred 30 minutes, and concentrated. Meanwhile, to a solution of the oxazolidinone (2.64 g, 14.9 mmol) in 40 mL THF at −78° C. was added n-butyllithium (1.6 M soln in hexanes, 9.3 mL, 14.9 mmol) dropwise. The mixture was stirred for 10 minutes at which time the acid chloride in 10 mL THF was added dropwise. The reaction was stirred 30 minutes at −78° C., then warmed directly to ambient temperature and quenched with sat. NH4Cl. The mixture was partitioned between Et2O and sat. NH4Cl (aq), the phases were separated, and the organic phase dried (MgSO4), and concentrated to furnish 3.2 g of the titled compound as a colorless oil. LRMS: m/z 318.2 (M+).

Aufarbeitung

  1. customresulting in vigorous gas evolution
  2. concentrationconcentrated
  3. additionwas added dropwise
  4. stirringThe reaction was stirred 30 minutes at −78° C.
  5. temperaturewarmed directly to ambient temperature
  6. customquenched with sat. NH4Cl
  7. customThe mixture was partitioned between Et2O and sat. NH4Cl (aq)
  8. customthe phases were separated
  9. dry with materialthe organic phase dried (MgSO4)
  10. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9f3f8c1207324e59877635d1c4946a49
Quelldatensatz
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07419981B2

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