Reaktion #66547

ord-1732818959bb4e6aa79ac33906d948fb

Reaktionsgleichung

CN(C)C(On1nnc2cccnc21)=[N+](C)C.F[P-](F)(F)(F)(F)F
HATU
C[C@H]1CN(C(=O)OC(C)(C)C)CCN1
3-Methyl-(3S)-1-piperazinecarboxylic acid, 1,1-dimethylethyl ester
O=C(O)Cc1ccccc1
benzeneacetic acid
CCN(C(C)C)C(C)C
Hunigs base
→
C[C@H]1CN(C(=O)OC(C)(C)C)CCN1C(=O)Cc1ccccc1
sub-title compound
Ausbeute 83.0%
C[C@H]1CN(C(=O)OC(C)(C)C)CCN1C(=O)Cc1ccccc1
3-Methyl-4-(phenylacetyl)-(3S)-1-piperazinecarboxylic Acid, 1,1-dimethylethyl Ester
Ausbeute 83.0%

Edukte

CN(C)C(On1nnc2cccnc21)=[N+](C)C.F[P-](F)(F)(F)(F)F
HATU
C[C@H]1CN(C(=O)OC(C)(C)C)CCN1
3-Methyl-(3S)-1-piperazinecarboxylic acid, 1,1-dimethylethyl ester
O=C(O)Cc1ccccc1
benzeneacetic acid
CCN(C(C)C)C(C)C
Hunigs base

Reagenzien

Keine

Lösungsmittel

CCOC(C)=O
EtOAc
CN(C)C=O
DMF

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Waschenwashed with water and brine
  2. 2
    Trocknendried (MgSO4)
  3. 3
    Einengenconcentrated in vacuo
  4. 4
    SonstigeThe residue was purified by chromatography on silica with 25% EtOAc/isohexane as eluent

Vorschrift

3-Methyl-(3S)-1-piperazinecarboxylic acid, 1,1-dimethylethyl ester (250 mg), benzeneacetic acid (210 mg) and Hunigs base (450 □l) were dissolved in DMF (10 ml) and HATU (720 mg) added portionwise over 2 min. The reaction mixture was stirred for 3 h, diluted with EtOAc, washed with water and brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by chromatography on silica with 25% EtOAc/isohexane as eluent to give the sub-title compound (330 mg)

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08524715B2uspto-grants-2013_09