Dimethyl Sulfoxide → 2-Methyl-3-[(S)-5-oxo-1-((S)-1-phenyl-ethyl)-pyrrolidin-3-yl]-propionic Acid Methyl Ester

HRID 130528

Reaktionsgleichung

Reaktionsgleichung von HRID 130528
[CH3:1][O:2][C:3](=[O:25])[C:4](C)([CH2:9][C@H:10]1[CH2:14][C:13](=[O:15])[N:12]([C@H:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH3:17])[CH2:11]1)[C:5](OC)=O.[Na+].[Cl-].CS(C)=O>O>[CH3:1][O:2][C:3](=[O:25])[CH:4]([CH3:5])[CH2:9][C@H:10]1[CH2:14][C:13](=[O:15])[N:12]([C@H:16]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH3:17])[CH2:11]1

Komponenten

5

Edukt 3

HCID 679Dimethyl SulfoxideHCID 5234Sodium ChlorideHCID 590940412-Methyl-2-[(S)-5-oxo-1-((S)-1-phenyl-ethyl)-pyrrolidin-3-ylmethyl]-malonic Acid Dimethyl Ester

Produkt 1

HCID 590940382-Methyl-3-[(S)-5-oxo-1-((S)-1-phenyl-ethyl)-pyrrolidin-3-yl]-propionic Acid Methyl EsterAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

The ester 92 (483 mg, 1.4 mmol), NaCl (104 mg, 1.8 mmol), water (105 μL) and DMSO (5 mL) were heated to reflux for 2 hours. The solution was cooled to room temperature water was added and the aqueous solution extracted with ether. The combined organic extracts were dried (MgSO4) and concentrated. Flash chromatography (80% to 66% hexane/acetone) of the residue gave the product as an oil (160 mg, 40%). MS m/z 290 (M+H, 100%).

Aufarbeitung

  1. temperatureto reflux for 2 hours
  2. additionwas added
  3. extractionthe aqueous solution extracted with ether
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-94e30271c0844e1692e7ab625415e2df
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07381747B2

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