Dicyclohexylcarbodiimide → 4-(2,5-Anhydro-4-bromo-3,4-dideoxy-D-erythropentonoyl)-1-piperazinecarboxylic acid phenylmethyl ester

HRID 54789

Reaktionsgleichung

Reaktionsgleichung von HRID 54789
[Br:1][C@@H:2]1[CH2:9][O:8][C@@H:4]([C:5]([OH:7])=O)[CH2:3]1.ON1C2C=CC=CC=2N=N1.[CH2:20]([O:27][C:28]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C1(N=C=NC2CCCCC2)CCCCC1>O.CN(C)C=O.C(Cl)Cl>[C:21]1([CH2:20][O:27][C:28]([N:30]2[CH2:35][CH2:34][N:33]([C:5]([C@@H:4]3[O:8][CH2:9][C@@H:2]([Br:1])[CH2:3]3)=[O:7])[CH2:32][CH2:31]2)=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

8

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 643495Benzyl piperazine-1-carboxylateHCID 67648725HCID 67648725, Verbindung

Produkt 1

HCID 1317198554-(2,5-Anhydro-4-bromo-3,4-dideoxy-D-erythropentonoyl)-1-piperazinecarboxylic acid phenylmethyl esterAusbeute 57,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 0.941 g of product from Example 150, 0.652 g of 1-hydroxybenzotriazole, 1.17 g of 1-benzyloxycarbonyl piperazine, 1.39 g of dicyclohexylcarbodiimide and 8 ml of dry methylene chloride is stirred at room temperature for 1 hour. Five ml of dimethylformamide is added and the stirring continued overnight at room temperature. The reaction mixture is diluted with water and extracted with chloroform. The organic layer is dried, concentrated in vacuo and the residue purified by chromatography (silica gel: 10-80% ethyl acetate/hexane) to give 1.1 g of the desired product.

Aufarbeitung

  1. customthe stirring continued overnight
  2. customat room temperature
  3. extractionextracted with chloroform
  4. customThe organic layer is dried
  5. concentrationconcentrated in vacuo
  6. customthe residue purified by chromatography (silica gel: 10-80% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-d23b9cb991464243b285bc1e2e58ccff
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05623081

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