(2S)-4-amino-2-(((tert-butoxy)carbonyl)amino)butanoic acid → (S,S)-2,7-Bis(tert-butyloxycarbonylamino)-4-azaoctanedioic acid

HRID 976023Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 976023
[NH2:1][CH2:2][CH2:3][C@H:4]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:5]([OH:7])=[O:6]>C(#N)C>[C:12]([O:11][C:9]([NH:8][C@@H:4]([CH2:3][NH:1][CH2:2][CH2:3][C@H:4]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:5]([OH:7])=[O:6])[C:5]([OH:7])=[O:6])=[O:10])([CH3:15])([CH3:13])[CH3:14]

Komponenten

3

Edukt 1

HCID 7019666(2S)-4-amino-2-(((tert-butoxy)carbonyl)amino)butanoic acid

Produkt 1

HCID 57285280(S,S)-2,7-Bis(tert-butyloxycarbonylamino)-4-azaoctanedioic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

A solution of (S)-4-amino-2-tert-butyloxycarbonylaminobutyric acid (1.03 g, 4.70 mmol) in acetonitrile (50 ml) was added to a solution of (S)-Boc-serine-β-lactone (0.80 g, 4.27 mmol) in acetonitrile (50 ml) and degassed H2O (50 ml). The pH was maintained at 5.5 by dropwise addition of 1M NaHCO3 with stirring. The mixture was stirred for 5 days at ambient temperature. The pH was controlled by NaHCO3 addition and the reaction monitored by TLC. The solvents were distilled off, the residue triturated with chloroform (5 ml), to which acetic acid was added to give pH 5. The chloroform solution was evaporated and the product isolated after chromatography on silica gel (CHCl3:MeOH 2:1).

Aufarbeitung

  1. customdegassed H2O (50 ml)
  2. temperatureThe pH was maintained at 5.5 by dropwise addition of 1M NaHCO3
  3. stirringThe mixture was stirred for 5 days at ambient temperature
  4. additionThe pH was controlled by NaHCO3 addition
  5. distillationThe solvents were distilled off
  6. customthe residue triturated with chloroform (5 ml), to which acetic acid
  7. additionwas added
  8. customto give pH 5
  9. customThe chloroform solution was evaporated
  10. customthe product isolated after chromatography on silica gel (CHCl3:MeOH 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-ba29660763804d9eb3abe48ee51f82d8
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05610141

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