Dimethyl Sulfoxide → (2s,4r)-n-Tert-butoxycarbonyl-4-(n-tert-butoxycarbonylglycylamino)-2-pyrrolidinecarboxaldehyde

HRID 2185497Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2185497
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]([O:15][C:16]([N:18]1[CH2:22][C@H:21]([NH:23][C:24](=[O:34])[CH2:25][NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:20][C@H:19]1[CH2:35][OH:36])=[O:17])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>ClCCl>[C:11]([O:15][C:16]([N:18]1[CH2:22][C@H:21]([NH:23][C:24](=[O:34])[CH2:25][NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:20][C@H:19]1[CH:35]=[O:36])=[O:17])([CH3:13])([CH3:14])[CH3:12]

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 70172939(2s,4r)-4-(n-Tert-butoxycarbonylglycylamino)-2-hydroxymethyl-n-tert-butoxycarbonylpyrrolidine

Produkt 1

HCID 73947491(2s,4r)-n-Tert-butoxycarbonyl-4-(n-tert-butoxycarbonylglycylamino)-2-pyrrolidinecarboxaldehydeAusbeute 97,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

The following reaction was carried under argon. Dimethyl sulfoxide (288 μL) was added to a stirred solution of oxalyl chloride (177 mL) in dichloromethane (3 mL) at −78° C. After stirring at the same temperature for 15 min, a solution of (2S,4R)-N-tert-butoxycarbonyl-4-(N-tert-butoxycarbonylglycylamino)-2-hydroxymethylpyrrolidine (151 mg) in dichloromethane (3 mL) was added. The mixture was stirred at −78° C. for 2 hr, and triethylamine (848 μL) was added to the reaction mixture. The mixture was stirred at 0° C. for 1 hr, quenched with saturated ammonium chloride, and extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform then chloroform:methanol=99:1 to 97:3, v/v) to give the titled compound (147 mg) as a colorless foam.

Aufarbeitung

  1. customThe following reaction
  2. stirringThe mixture was stirred at −78° C. for 2 hr
  3. stirringThe mixture was stirred at 0° C. for 1 hr
  4. customquenched with saturated ammonium chloride
  5. extractionextracted with dichloromethane
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by silica gel column chromatography (chloroform

Quellen und Nachweise

ORD-Eintrag
ord-03fc29335e094994a8fa838f145795ca
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06399629B1

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