Pyrrole-2-Carboxylic Acid → (Pyrrole-2-carbonyl)-N-(benzyl)glycine-t-butyl ester

HRID 362188Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 362188
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=O.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.CCN(C(C)C)C(C)C.[C:33]([O:37][C:38](=[O:48])[CH2:39][NH:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([CH3:36])([CH3:35])[CH3:34]>ClCCl.C(OCC)(=O)C>[C:33]([O:37][C:38](=[O:48])[CH2:39][N:40]([C:6]([C:2]1[NH:1][CH:5]=[CH:4][CH:3]=1)=[O:8])[CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([CH3:36])([CH3:34])[CH3:35]

Komponenten

7

Edukt 4

HCID 12473Pyrrole-2-Carboxylic AcidHCID 81531DiisopropylethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 11020442Tert-butyl 2-(benzylamino)acetate

Produkt 1

HCID 70020108(Pyrrole-2-carbonyl)-N-(benzyl)glycine-t-butyl esterAusbeute 34,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a suspension containing 3.00 g (27.0 mmol) of pyrrole-2-carboxylic acid in 75 mL of anhydrous dichloromethane under a nitrogen atmosphere at 0° C. was added 6.96 g (27.0 mmol of BOPCl and 14.1 mL (81.0 mmol) of DIEA. After stirring for 30 minutes, 5.97 g (27.0 mmol) of N-(benzyl)glycine-t-butyl ester was added and the reaction allowed to warm to room temperature overnight. The reaction was diluted with ethyl acetate and washed with a 5% potassium hydrogensulfate, saturated sodium bicarbonate solution and brine. The organic phase was dried over magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using a gradient of 100% hexane to 60% hexane/ethyl acetate to afford 2.92 g (34.4%) of the title compound is a white solid. FAB MS [M+H] m/z Calcd: 315, Found: 315.

Aufarbeitung

  1. washwashed with a 5% potassium hydrogensulfate, saturated sodium bicarbonate solution and brine
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel using a gradient of 100% hexane to 60% hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-1820661c54d14ba98f6fd55107381985
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05869455

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