Reaktion #4519

ord-34b5a02bca8a409287c4f086e8e5d348

Reaktionsgleichung

CCCCCCCCCCCCCCCC(=O)N[C@@H](C)C(=O)N[C@H](CCC(=O)O)C(=O)OCc1ccccc1
palmitoyl-L-Ala-D-Glu(OH)OBzl
O=C1CCC(=O)N1O
N-hydroxysuccinimide
C(=NC1CCCCC1)=NC1CCCCC1
dicyclohexylcarbodiimide
CCCCCCCCCCCCCCCC(=O)N[C@@H](C)C(=O)N[C@H](CCC(=O)ON1C(=O)CCC1=O)C(=O)OCc1ccccc1
palmitoyl-L-Ala-D-Glu(OSu)OBzl

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Filtrationthe precipitate was filtered off
  2. 2
    Waschenwashed with chloroform
  3. 3
    EinengenThe filtrate was concentrated in vacuo
  4. 4
    workup.ADDITIONthe diisopropylether was added to the residue
  5. 5
    SonstigeThe product was collected
  6. 6
    Sonstigedried

Vorschrift

To a solution of palmitoyl-L-Ala-D-Glu(OH)OBzl (1)(1.84 g) in a mixture of tetrahydrofuran (20 ml) and chloroform (30 ml) were added N-hydroxysuccinimide (425 mg) and dicyclohexylcarbodiimide (728 mg). The reaction mixture was kept for 18 hours at room temperature and the precipitate was filtered off and washed with chloroform. The filtrate was concentrated in vacuo and the diisopropylether was added to the residue. The product was collected and dried to afford palmitoyl-L-Ala-D-Glu(OSu)OBzl (2)(170 g).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04725582uspto-grants-1988_02