1-Piperazinecarboxylic acid, ethyl ester → 4-((S)-4-Benzyloxy-2-tert-butoxycarbonylamino-butyryl)-piperazine-1-carboxylic acid ethyl ester

HRID 1185464Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1185464
[CH2:1]([O:8][CH2:9][CH2:10][C@H:11]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:12]([OH:14])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.[CH2:45]([O:47][C:48]([N:50]1[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]1)=[O:49])[CH3:46].C(=O)([O-])O.[Na+]>CN(C=O)C>[CH2:45]([O:47][C:48]([N:50]1[CH2:51][CH2:52][N:53]([C:12](=[O:14])[C@@H:11]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:10][CH2:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:54][CH2:55]1)=[O:49])[CH3:46]

Komponenten

6

Edukt 4

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 516892Sodium BicarbonateHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 15058464O-Benzyl-N-(tert-butoxycarbonyl)-L-homoserine

Produkt 1

HCID 668557344-((S)-4-Benzyloxy-2-tert-butoxycarbonylamino-butyryl)-piperazine-1-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 220 mg of (S)-4-Benzyloxy-2-tert-butoxycarbonylamino-butyric acid, 327 mg of NEM and 233 mg of TOTU in 1.6 ml of DMF, 112 mg of Piperazine-1-carboxylic acid ethyl ester was added at RT and stirred for 16 h. The reaction mixture was diluted saturated aqueous sodium hydrogen carbonate solution. After filtration through a chem Elut® cartridge by eluting with ethyl acetate the solvents were removed under reduced pressure. The isolated crude product was pure enough for the next reaction step.

Aufarbeitung

  1. filtrationAfter filtration through a chem Elut® cartridge
  2. washby eluting with ethyl acetate the solvents
  3. customwere removed under reduced pressure
  4. customThe isolated crude product
  5. customwas pure enough for the next reaction step

Quellen und Nachweise

ORD-Eintrag
ord-44ede83fbdd24e6c953a302ab0a9ddf1
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08669266B2

Notizen zur Reaktion

Wird geladen…