Reaktion #2150630

ord-51d88012dbf54d53990a2407af394703

Reaktionsgleichung

O=C([O-])O.[Na+]
NaHCO3
CC(C)(C)OC(=O)CC[C@H](NC(=O)OCc1ccccc1)C(=O)O
Cbz-(L)Glu(OtBu)-OH
O.On1nnc2ccccc21
HOBT hydrate
CCN=C=NCCCN(C)C.Cl
EDCI hydrochloride
CCN(C(C)C)C(C)C
DIPEA
→
CCCCOC(=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 butyl ester

Edukte

O=C([O-])O.[Na+]
NaHCO3
CC(C)(C)OC(=O)CC[C@H](NC(=O)OCc1ccccc1)C(=O)O
Cbz-(L)Glu(OtBu)-OH
O.On1nnc2ccccc21
HOBT hydrate
CCN=C=NCCCN(C)C.Cl
EDCI hydrochloride
CCN(C(C)C)C(C)C
DIPEA
—
intermediate 1.4

Reagenzien

Keine

Lösungsmittel

ClCCl
DCM
C1CCOC1.ClCCl
DCM THF

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigethe phases were separated
  2. 2
    Waschenphase was washed with a 1M NaHSO4 solution
  3. 3
    Trocknendried (Na2SO4)
  4. 4
    Sonstigeevaporated off

Vorschrift

Cbz-(L)Glu(OtBu)-OH (10 g), HOBT hydrate (5 g), EDCI hydrochloride (6.3 g), intermediate 1.4 (6 g) and DIPEA (10 mL) were dissolved in DCM/THF (1/1, 84 mL). The mixture was stirred at RT for 1 h. DCM and an aq. NaHCO3 solution were added to the mixture and the phases were separated. The org. phase was washed with a 1M NaHSO4 solution, dried (Na2SO4) and evaporated off. CC of the crude (EA/Hept 1/2) offered 13.8 g of the desired compound.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08288385B2uspto-grants-2012_10