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Sulfuric Acid → tert-Butyl 5-oxo-L-prolinate

HRID 469727
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 469727
[NH:1]1[C@H:5]([C:6]([OH:8])=[O:7])[CH2:4][CH2:3][C:2]1=[O:9].[CH3:10][C:11]([CH3:13])=[CH2:12].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>ClCCl>[C:11]([O:7][C:6]([C@@H:5]1[CH2:4][CH2:3][C:2](=[O:9])[NH:1]1)=[O:8])([CH3:13])([CH3:12])[CH3:10]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 1118Sulfuric AcidHCID 7405L-Pyroglutamic AcidHCID 8255IsobutyleneHCID 516892Sodium Bicarbonate

Produkt 1

HCID 10888648tert-Butyl 5-oxo-L-prolinate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A pressure flask is charged with (S)-(−)-2-pyrrolidone-5-carboxylic acid (25 g, 193.6 mmol) and dichloromethane (100 mL) and the stirred suspension is cooled in a dry ice acetone bath. Liquid 2-methylpropene (150 mL) is added followed by concentrated sulfuric acid (0.5 mL). The pressure flask is sealed and the reaction mixture is stirred at room temperature for 48 h. The pressure flask is cooled in a dry acetone bath and the reaction mixture is diluted with dichloromethane (500 mL) and treated with a saturated solution of sodium bicarbonate until the effervescence is ceased. The organic layer is separated, washed with saturated solution of sodium bicarbonate (300 mL), brine (300 mL), dried over anhydrous Na2SO4 and solvent removed in vacuo to give the title compound as a white crystalline solid. The crude material is used without purification.

Aufarbeitung

  1. temperaturethe stirred suspension is cooled in a dry ice acetone bath
  2. customThe pressure flask is sealed
  3. temperatureThe pressure flask is cooled in a dry acetone bath
  4. customThe organic layer is separated
  5. washwashed with saturated solution of sodium bicarbonate (300 mL), brine (300 mL)
  6. dry with materialdried over anhydrous Na2SO4 and solvent
  7. customremoved in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7e41d20859be4bfcb5f33e9458184f62
Quelldatensatz
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08629157B2

Notizen zur Reaktion

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