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

HRID 327822

Reaktionsgleichung

Reaktionsgleichung von HRID 327822
[NH2:1][N:2]1[CH:6]=[CH:5][CH:4]=[CH:3]1.[C:7]([NH:17][C@H:18]([C:21](O)=[O:22])[CH2:19][OH: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][C@@H:18]([CH2:21][OH:22])[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 100310N-(Benzyloxycarbonyl)-L-serineHCID 1365891-Aminopyrrole

Produkt 1

HCID 10979597(S)-Phenylmethyl-[1-(hydroxymethyl)-2-oxo-2-(1H-pyrrol-1-ylamino)ethyl]carbamateAusbeute 61,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1-aminopyrrole (3.28 g) and carbobenzyloxy-L-serine (9.57 g) in 100 ml of dry DCM and 10 ml of dry dimethylformamide was added DCC (10.0 g) at 0° C. After 10 minutes the ice bath was removed and the reaction mixture was stirred at room temperature overnight. The precipitate was filtered 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). The appropriate fractions were concentrated and the residue recrystallized from ethyl acetate to afford 7.48 g of the product as crystals, m.p. 163°-164° C.

Aufarbeitung

  1. customAfter 10 minutes the ice bath was removed
  2. filtrationThe precipitate was filtered
  3. stirringstirred
  4. filtrationThe mixture was filtered
  5. customevaporated to dryness
  6. customThe residue was purified by flash column chromatography (silica gel, DCM/methanol 20:1)
  7. concentrationThe appropriate fractions were concentrated
  8. customthe residue recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-c01bbdaad14e4e3cb478d7e9e39f6654
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05274116

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