Reaktion #531899

ord-649de971eeb042819bc352c3c850f95c

Reaktionsgleichung

NC(=O)[C@H](N)CCC(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)O
H-D-iGlu-D-Trp-OH
NC(=O)[C@H](N)CCC(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)O
D-isoglutamyl-D-tryptophan
[NH4+].[OH-]
ammonium hydroxide
[NH4+].[OH-]
Ammonium hydroxide
NC(=O)[C@H](N)CCC(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)[O-].[NH4+]
D-isoglutamyl-D-tryptophan, ammonium salt

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeVolatile materials were removed in vacuo
  2. 2
    workup.ADDITIONthe residual oil was mixed with isopropanol
  3. 3
    Filtrationthe solid ammonium salt was collected by suction filtration
  4. 4
    SonstigeThe solid was dried to constant weight (1 g) under high vacuum for 12 h

Vorschrift

H-D-iGlu-D-Trp-OH (1 g from Example 3) was mixed with ammonium hydroxide (0.55M, 6 mL). The mixture was stirred and the pH was measured to be around 4.5. Ammonium hydroxide (0.55M) was added dropwise until the pH of the solution reached between 7.0 to 7.5. Volatile materials were removed in vacuo, and the residual oil was mixed with isopropanol. A white precipitate appeared. After 2 h, the solid ammonium salt was collected by suction filtration. The solid was dried to constant weight (1 g) under high vacuum for 12 h to give the D-isoglutamyl-D-tryptophan, ammonium salt (1:1). The water content as determined by the Karl-Fisher test was 4.6%.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08476235B2uspto-grants-2013_07