Acetonitrile → Boc-Dap-OH

HRID 1055258

Reaktionsgleichung

Reaktionsgleichung von HRID 1055258
[C:1]([NH:8][C@H:9]([C:14]([OH:16])=[O:15])[CH2:10]C(=O)N)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CCOC(C)=O.C(#[N:25])C.CC(OI(OC(C)=O)C1C=CC=CC=1)=O>O>[NH:8]([C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[C@H:9]([C:14]([OH:16])=[O:15])[CH2:10][NH2:25]

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 76724Iodobenzene diacetateHCID 82035N2-((tert-Butoxy)carbonyl)-L-asparagine

Produkt 1

HCID 2755946Boc-Dap-OHAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
16 °C

Versuchsvorschrift

A slurry of N-Boc-L-asparagine (5.00 g, 21.5 mmol), EtOAc (24 mL), acetonitrile (24 mL), water (12 mL), and PIDA (8.32 g, 25.8 mmol) was cooled and stirred at 16° C. for 30 min. The temperature was then allowed to reach 20° C., and the reaction was stirred until completion (ca. 4 h). The mixture was cooled to 0° C. and filtered. The filter cake was washed with EtOAc (10 mL) and dried in vacuo to give 1 (2.73 g, 62% yield). 1H NMR (CD3OD and a drop of TFA) δ4.05 (1H), 3.20-3.08 (2H), 1.45 (9H).

Aufarbeitung

  1. customto reach 20° C.
  2. stirringthe reaction was stirred until completion (ca. 4 h)
  3. temperatureThe mixture was cooled to 0° C.
  4. filtrationfiltered
  5. washThe filter cake was washed with EtOAc (10 mL)
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-04c0041e90df4b09b95c11870fd224cd
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394338B2

Verknüpfte Notizen

Wird geladen…