tert-Butyl (2S)-2-amino-3-(4-(3-ethoxycarbonylpropyloxy)phenyl)propionate → (1,1-dimethyl ethyl) N-(5-bromo-7-fluoro-2-benzoxazolyl)-O-(4-ethoxy-4-oxo-butyl)-L-tyrosinate

HRID 1759712Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1759712
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:24]=[CH:23][C:12]([CH2:13][C@@H:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[NH2:15])=[CH:11][CH:10]=1)[CH3:2].[Br:26][C:27]1[CH:28]=[C:29]([F:38])[C:30]2[O:34][C:33](SC)=[N:32][C:31]=2[CH:37]=1>C([O-])(=O)C.C([O-])(=O)C.[Hg+2]>[Br:26][C:27]1[CH:28]=[C:29]([F:38])[C:30]2[O:34][C:33]([NH:15][C@H:14]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[CH2:13][C:12]3[CH:11]=[CH:10][C:9]([O:8][CH2:7][CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:25])=[CH:24][CH:23]=3)=[N:32][C:31]=2[CH:37]=1

Komponenten

4

Edukt 2

HCID 15512208tert-Butyl (2S)-2-amino-3-(4-(3-ethoxycarbonylpropyloxy)phenyl)propionateHCID 225994905-Bromo-7-fluoro-2-(methylthio)-benzoxazole

Produkt 1

HCID 69880648(1,1-dimethyl ethyl) N-(5-bromo-7-fluoro-2-benzoxazolyl)-O-(4-ethoxy-4-oxo-butyl)-L-tyrosinateAusbeute 40,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 15337Mercuric acetateKatalysator

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

The mixture constituted by aminoester 4-2 (865 mg; 2.46 mmoles), 5-bromo-7-fluoro-2-(methylthio)-benzoxazole (804 mg; 3.07 mmoles) and mercury diacetate (437 mg) is agitated for 3 hours, under nitrogen and at 100° C. After cooling down, the medium is chromatographed eluting with a CH2Cl2/ethyl acetate mixture 95/5, 564 mg of expected product is obtained, which is repurified by recrystallizing from isopropyl oxide. 528 mg of purified product is obtained.

Aufarbeitung

  1. temperatureAfter cooling down
  2. customthe medium is chromatographed
  3. washeluting with a CH2Cl2/ethyl acetate mixture 95/5

Quellen und Nachweise

ORD-Eintrag
ord-57cb84ae0b3540efbaee501e8b58cb22
Quelldatensatz
uspto-grants-2005_01
Patentnummer
US06838453B2

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