3-Amino-1-propanol → (2-(2-Benzyloxycarbonylamino-ethoxy)-ethyl)-carbamic acid benzyl ester

HRID 1387252Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1387252
[CH2:1](CO)[CH2:2][NH2:3].[CH2:6]([O:13][C:14]([NH:16][CH2:17][CH2:18][OH:19])=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:20]12([CH2:30]S(O)(=O)=O)C(C)(C)[CH:24]([CH2:25][CH2:26]1)[CH2:23][C:21]2=O.[C:35](=O)([OH:37])[O-:36].[Na+]>O1CCOCC1.CN(C=O)C.CS(C)=O>[CH2:6]([O:13][C:14]([NH:16][CH2:17][CH2:18][O:19][CH2:1][CH2:2][NH:3][C:35]([O:37][CH2:30][C:20]1[CH:21]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:36])=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

6

Edukt 4

HCID 90863-Amino-1-propanolHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 280458benzyl N-(2-hydroxyethyl)carbamateHCID 516892Sodium Bicarbonate

Produkt 1

HCID 3090849(2-(2-Benzyloxycarbonylamino-ethoxy)-ethyl)-carbamic acid benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 86757220HCID 86757220, VerbindungLösungsmittel

Versuchsvorschrift

The propanolamine compound prepared above (1.0 eq), N-(benzyloxycarbonyl)ethanolamine (25 eq) and camphorsulfonic acid (1.0 eq) are dissolved in a small amount of dioxane-DMF-DMSO (10:2:1) and stirred at room temperature for about 24 hours. The mixture is neutralized by the addition of aqueous sodium bicarbonate and purified by preparative HPLC (C18 “ZORBAX”, step gradient starting at 70/30:H2O/CH3CN/0.1% TFA). The appropriate fractions are combined, frozen and lyophilized to give solid (MW=1621.66).

Aufarbeitung

  1. custompurified by preparative HPLC (C18 “ZORBAX”, step gradient starting at 70/30:H2O/CH3CN/0.1% TFA)
  2. temperaturefrozen
  3. customto give solid (MW=1621.66)

Quellen und Nachweise

ORD-Eintrag
ord-24f0246d17ef4387b2f4f1c609615fb6
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06268338B1

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