Serinol → BOC-D-Ala-SerOH

HRID 36578

Reaktionsgleichung

Reaktionsgleichung von HRID 36578
C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N([OH:25])N=NC=2C=1.[NH:26]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C@@H:27]([C:29]([OH:31])=O)[CH3:28].[NH2:39][CH:40]([CH2:43][OH:44])[CH2:41][OH:42]>>[NH:26]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C@@H:27]([C:29]([NH:39][C@H:40]([C:43]([OH:25])=[O:44])[CH2:41][OH:42])=[O:31])[CH3:28]

Komponenten

4

Edukt 3

HCID 68294SerinolHCID 637606BOC-D-alanineHCID 21712060DCCI HOBt

Produkt 1

HCID 131719002BOC-D-Ala-SerOH

Versuchsvorschrift

BOC-D-Ala-SerOH was prepared on a 1.0 mMol-scale by the DCC-HOBT mediated condensation of BOC-D-Ala and serinol following the procedure described in Example 21. The crude reaction product was purified by chromatography on a 1.7×24 cm column of BioSil A by successive elution with (A) 100 ml CHCl3, (B) 100 ml of 1% (v/v) MeOH/CHCl3, (C) 100 ml of 2% MeOH/CHCl3, (D) 100 ml of 4% MeOH/CHCl3, (E) 100 ml of 8% MeOH/CHCl3, and (F) 100 ml of 12% MeOH/CHCl3. The appropriate column fractions were combined and concentrated to dryness on the rotary evaporator. The oily residue was then taken up in 10 ml of CH2Cl2, filtered from the small amount of insoluble material, and again concentrated to dryness. The residue was further dried under high vacuum to yield 168 mg (68%) of product as a colorless viscous oil.

Aufarbeitung

  1. customThe crude reaction product
  2. customwas purified by chromatography on a 1.7×24 cm column of BioSil A by successive elution with (A) 100 ml CHCl3, (B) 100 ml of 1% (v/v) MeOH/CHCl3, (C) 100 ml of 2% MeOH/CHCl3, (D) 100 ml of 4% MeOH/CHCl3, (E) 100 ml of 8% MeOH/CHCl3, and (F) 100 ml of 12% MeOH/CHCl3
  3. concentrationconcentrated to dryness on the rotary evaporator
  4. filtrationfiltered from the small amount of insoluble material
  5. concentrationagain concentrated to dryness
  6. customThe residue was further dried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-11734697bc8b4862a4a8b9e8de514a85
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05416070

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