Water → methyl (S)-2-cyclopropylmethoxy-3-[3'-(methylamino)biphenyl-4-yl]propanoate

HRID 1009222Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1009222
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@H:9]([O:14][CH2:15][CH:16]2[CH2:18][CH2:17]2)[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[CH3:19][NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23](B2OC(C)(C)C(C)(C)O2)[CH:22]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:16]1([CH2:15][O:14][C@@H:9]([CH2:8][C:5]2[CH:6]=[CH:7][C:2]([C:23]3[CH:24]=[CH:25][CH:26]=[C:21]([NH:20][CH3:19])[CH:22]=3)=[CH:3][CH:4]=2)[C:10]([O:12][CH3:13])=[O:11])[CH2:18][CH2:17]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 57976762N-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 67304435methyl (S)-3-(4-bromophenyl)-2-(cyclopropylmethoxy)propanoate

Produkt 1

HCID 67304613methyl (S)-2-cyclopropylmethoxy-3-[3'-(methylamino)biphenyl-4-yl]propanoateAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

53 mg (0.046 mmol) of tetrakis(triphenylphosphine)palladium are added to a solution of 145 mg (0.46 mmol) of methyl (S)-3-(4-bromophenyl)-2-(cyclopropylmethoxy)propionate and 129 mg (0.55 mmol) of methyl[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]amine in 3 ml of dimethylformamide. 0.3 ml of a 2M potassium phosphate solution is added and the reaction mixture is stirred at 90° C. for 2 hours. The reaction is halted by the addition of 10 ml of water and then extraction is carried out with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated and then the residue is chromatographed on silica gel (heptane/ethyl acetate 80/20). 70 mg of methyl (S)-2-cyclopropylmethoxy-3-[3′-(methylamino)biphenyl-4-yl]propanoate are obtained in the form of an oil. Yield=45%.

Aufarbeitung

  1. extractionextraction
  2. dry with materialdried over sodium sulfate
  3. customThe solvents are evaporated
  4. customthe residue is chromatographed on silica gel (heptane/ethyl acetate 80/20)

Quellen und Nachweise

ORD-Eintrag
ord-cfbcca531459448da90bca1d35b9367b
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973063B2

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