Ethylmorpholine → 4-(2-Benzyloxycarbonylamino-3-fluoro-butyryl)-piperazine-1-carboxylic acid propyl ester

HRID 1970573Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1970573
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH:16]([F:18])[CH3:17])[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]([O:22][C:23]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)=[O:24])[CH2:20][CH3:21].C(N1CCOCC1)C.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O>CN(C=O)C.C(OCC)(=O)C>[CH2:19]([O:22][C:23]([N:25]1[CH2:30][CH2:29][N:28]([C:13](=[O:15])[CH:12]([NH:11][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH:16]([F:18])[CH3:17])[CH2:27][CH2:26]1)=[O:24])[CH2:20][CH3:21]

Komponenten

7

Edukt 4

HCID 7525EthylmorpholineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 22393735Propyl piperazine-1-carboxylateHCID 668548062-Benzyloxycarbonylamino-3-fluoro-butyric acid

Produkt 1

HCID 668548184-(2-Benzyloxycarbonylamino-3-fluoro-butyryl)-piperazine-1-carboxylic acid propyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 500 mg 2-Benzyloxycarbonylamino-3-fluoro-butyric acid in 3 ml DMF were added 310 mg 1-propoxycarbonylpiperazine, 0.50 ml N-ethylmorpholine and 643 mg TOTU. After stirring for 12 h it was diluted with ethyl acetate and extracted with aqueous LiCl (4% w/w), aqueous NaHCO3, 0.1 M HCl and brine. The organic layer was dried over MgSO4 and concentrated to furnish the crude coupling product which was used without further purification in the next step. Yield: 591 mg

Aufarbeitung

  1. extractionextracted with aqueous LiCl (4% w/w), aqueous NaHCO3, 0.1 M HCl and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customto furnish the crude coupling product which
  5. customwas used without further purification in the next step

Quellen und Nachweise

ORD-Eintrag
ord-279bff66ce9c4b75838f84b3dfc0eff2
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426420B2

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