Triethylamine → [5-(4-Bromo-phenyl)-oxazol-4-yl]-carbamic acid (R)-1-phenyl-ethyl ester

HRID 919048Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 919048
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][CH:11]=[N:10][C:9]=2C(O)=O)=[CH:4][CH:3]=1.[C:16]1([C@H:22]([OH:24])[CH3:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([N:27]([CH2:30]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:39])C=CC=CC=1>C1(C)C=CC=CC=1>[C:16]1([C@H:22]([O:24][C:30](=[O:39])[NH:27][C:9]2[N:10]=[CH:11][O:12][C:8]=2[C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)[CH3:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 6375161-Phenylethanol, (R)-HCID 616374135-(4-Bromophenyl)oxazole-4-carboxylic acid

Produkt 1

HCID 67963772[5-(4-Bromo-phenyl)-oxazol-4-yl]-carbamic acid (R)-1-phenyl-ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

5-(4-Bromo-phenyl)-oxazole-4-carboxylic acid (0.5 g, 1.9 mmol), (R)-1-phenyl-ethanol (0.25 mL, 2.0 mmol) and triethylamine (0.55 mL, 3.8 mmol) were dissolved in toluene (10 mL). Diphenylphosphoryl azide (0.5 mL, 2.3 mmol) was added and the reaction was heated to 80° C. The reaction was monitored by analytical LCMS and when complete was cooled and submitted to standard aqueous workup. The crude material was purified on silica gel to provide the title compound.

Aufarbeitung

  1. temperaturecomplete was cooled
  2. customThe crude material was purified on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-35b3624a484f46eabe09acaf946b7d04
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09272990B2

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