Potassium Phosphate, Tribasic → HCID 57709015, Verbindung

HRID 547115Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 547115
[C:1]([Si:5]([O:8][CH:9]([CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([CH2:41][CH3:42])([C:25]2[CH:30]=[CH:29][C:28](B3OC(C)(C)C(C)(C)O3)=[C:27]([CH3:40])[CH:26]=2)[CH2:23][CH3:24])=[CH:18][C:17]=1[CH3:43])[C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:81][O:82][C:83](=[O:100])[C@@H:84]([NH:92][C:93]([O:95][C:96]([CH3:99])([CH3:98])[CH3:97])=[O:94])[C:85]1[CH:90]=[CH:89][C:88](Cl)=[CH:87][CH:86]=1>C1(C)C=CC=CC=1.O.C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:81][O:82][C:83](=[O:100])[C@@H:84]([NH:92][C:93]([O:95][C:96]([CH3:99])([CH3:98])[CH3:97])=[O:94])[C:85]1[CH:90]=[CH:89][C:88]([C:28]2[CH:29]=[CH:30][C:25]([C:22]([C:19]3[CH:20]=[CH:21][C:16]([CH2:15][CH2:14][CH:9]([O:8][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:6])[CH3:7])[C:10]([CH3:13])([CH3:12])[CH3:11])=[C:17]([CH3:43])[CH:18]=3)([CH2:23][CH3:24])[CH2:41][CH3:42])=[CH:26][C:27]=2[CH3:40])=[CH:87][CH:86]=1

Komponenten

9

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 577089262-[4-(1-{4-[3-(t-Butyldimethyl-silanyloxy)-4,4-dimethyl-pentyl]-3-methyl-phenyl}-1-ethyl-propyl)-2-methyl-phenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolaneHCID 57709120HCID 57709120, Verbindung

Produkt 1

HCID 57709015HCID 57709015, VerbindungAusbeute 67,4 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Degassed toluene (0.10 mL) was added to t-butyl-(1-{2-[4-(1-ethyl-1-{4-[4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl]-3-methyl-phenyl}-propyl)-2-methyl-phenyl]-ethyl}-2,2-dimethyl-propoxy)dimethylsilane (Example 24-(1); 25.2 mg, 0.0415 mmol), palladium (II) acetate (1.6 mg, 0.071 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (6.0 mg, 0.015 mmol) and potassium phosphate (24.5 mg, 0.115 mmol), and the mixture was stirred in a nitrogen atmosphere for three minutes. Then, a solution of (S)-t-butoxycarbonylamino-(4-chloro-phenyl)acetic acid methyl ester (Example 166-(1); 17.9 mg, 0.0597 mmol) in toluene (0.10 mL) and water (20 μL) were added, and the mixture was heated while stirring at an external temperature of 95 to 104° C. for one hour. The reaction mixture was diluted with diethyl ether and filtered through cotton plug, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=10/1) to give the title compound (20.8 mg, 67%).

Aufarbeitung

  1. customDegassed toluene (0.10 mL)
  2. temperaturethe mixture was heated
  3. stirringwhile stirring at an external temperature of 95 to 104° C. for one hour
  4. filtrationfiltered through cotton plug
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate=10/1)

Quellen und Nachweise

ORD-Eintrag
ord-bae52cf12cbe46aa8a28f7ded4aa8f72
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935688B2

Notizen zur Reaktion

Wird geladen…