Reaktion #505228

ord-ab5337ab9c34419089794c0202e6fccf

Reaktionsgleichung

CCOC(=O)N1CCNCC1
1-ethoxycarbonylpiperazine
CC(C)(C)OC(=O)CC[C@H](NC(=O)OCc1ccccc1)C(=O)O
Z-(L)Glu(OtBu)-OH
On1nnc2ccccc21
HOBT
CCN=C=NCCCN(C)C
EDCI
O=C([O-])O.[Na+]
NaHCO3
→
CCOC(=O)N1CCN(C(=O)[C@H](CCC(=O)OC(C)(C)C)NC(=O)OCc2ccccc2)CC1
desired compound
Ausbeute 98.9%
CCOC(=O)N1CCN(C(=O)[C@H](CCC(=O)OC(C)(C)C)NC(=O)OCc2ccccc2)CC1
4-((S)-2-benzyloxycarbonylamino-4-tert-butoxycarbonyl-butyryl)-piperazine-1-carboxylic acid ethyl ester
Ausbeute 98.9%

Edukte

CCOC(=O)N1CCNCC1
1-ethoxycarbonylpiperazine
CC(C)(C)OC(=O)CC[C@H](NC(=O)OCc1ccccc1)C(=O)O
Z-(L)Glu(OtBu)-OH
On1nnc2ccccc21
HOBT
CCN=C=NCCCN(C)C
EDCI
O=C([O-])O.[Na+]
NaHCO3

Reagenzien

Keine

Lösungsmittel

C1CCOC1.ClCCl
DCM THF
CCOC(C)=O
EA

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.WAITthe stirring was continued at RT overnight
  2. 2
    Sonstigethe phases were separated
  3. 3
    Waschenphase was washed with an aq. NaHSO4 (1M) solution and with brine
  4. 4
    Trocknendried over Na2SO4
  5. 5
    Sonstigeevaporated off
  6. 6
    SonstigeAfter HV drying

Vorschrift

To a solution of Z-(L)Glu(OtBu)-OH (5 g) in DCM/THF (1:1, 42 ml) were added at RT HOBT (2.5 g) and EDCI (3.1 g). After 15 min stirring at RT, 1-ethoxycarbonylpiperazine (2.6 g) was added and the stirring was continued at RT overnight. 150 ml of EA and 60 ml of a NaHCO3 solution were added to the reaction mixture and the phases were separated. The org. phase was washed with an aq. NaHSO4 (1M) solution and with brine, dried over Na2SO4 and evaporated off. After HV drying, 7 g of the desired compound were obtained.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08093250B2uspto-grants-2012_01