Dicyclohexylcarbodiimide → Phenylmethyl-[2-oxo-2-(1H-pyrrol-1-ylamino)ethyl]carbamate

HRID 327816

Reaktionsgleichung

Reaktionsgleichung von HRID 327816
[NH2:1][N:2]1[CH:6]=[CH:5][CH:4]=[CH:3]1.[C:7]([NH:17][CH2:18][C:19](O)=[O:20])([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C)C=O>[C:11]1([CH2:10][O:9][C:7](=[O:8])[NH:17][CH2:18][C:19](=[O:20])[NH:1][N:2]2[CH:6]=[CH:5][CH:4]=[CH:3]2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Komponenten

6

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 14349BenzyloxycarbonylglycineHCID 1365891-Aminopyrrole

Produkt 1

HCID 19973152Phenylmethyl-[2-oxo-2-(1H-pyrrol-1-ylamino)ethyl]carbamateAusbeute 18,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1-aminopyrrole (2.46 g) and carbobenzyloxyglycine (6.28 g) in 120 ml of dry DCM and 10 ml of dry dimethylformamide was added DCC (8.00 g). The reaction mixture was stirred at room temperature over a period of 64 hours. The precipitate was removed by filtration and stirred in boiling ethyl acetate. The mixture was filtered and the filtrate was combined with the filtrate of the reaction mixture and evaporated to dryness. The residue was purified by flash column chromatography (silica gel, DCM/methanol 20:1) yielding a first fraction (2.97 g) which was contaminated by DCU. A second fraction recrystallized from ethyl acetate afforded 1.54 g of the product as crystals, m.p. 146°-147° C.

Aufarbeitung

  1. customThe precipitate was removed by filtration
  2. stirringstirred
  3. filtrationThe mixture was filtered
  4. customevaporated to dryness
  5. customThe residue was purified by flash column chromatography (silica gel, DCM/methanol 20:1)
  6. customyielding a first fraction (2.97 g) which
  7. customA second fraction recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-d52ca637deaf4e8cb24303bd05bb79e5
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05274116

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