Chloride → Methyl 3-acetamido-4-(5-methoxycarbonyl-1-pentynyl)benzoate

HRID 278084

Reaktionsgleichung

Reaktionsgleichung von HRID 278084
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1OS(C(F)(F)F)(=O)=O)[C:8]([O:10][CH3:11])=[O:9])(=[O:3])[CH3:2].[C:23]([O:30][CH3:31])(=[O:29])[CH2:24][CH2:25][CH2:26][C:27]#[CH:28].[Cl-]>C(NCC)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[C:28]#[C:27][CH2:26][CH2:25][CH2:24][C:23]([O:30][CH3:31])=[O:29])[C:8]([O:10][CH3:11])=[O:9])(=[O:3])[CH3:2]

Komponenten

7

Edukt 3

HCID 312ChlorideHCID 534077Methyl 5-hexynoateHCID 14493070Methyl 3-acetamido-4-trifluoromethanesulfonyloxybenzoate

Produkt 1

HCID 22627137Methyl 3-acetamido-4-(5-methoxycarbonyl-1-pentynyl)benzoateAusbeute 86,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11776TriphenylphosphineKatalysatorHCID 24290Palladium ChlorideKatalysatorHCID 8021DiethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A mixture of methyl 3-acetamido-4-trifluoromethane-sulfonyloxybenzoate (1.43 g), methyl 5-hexynoate (582 mg), palladium(II) chloride (14 .9 mg), triphenylphosphine (43.8 mg) and cooper(I) chloride (32 mg) in diethylamine (18 ml) was stirred at 20° C. for 14 hours. The solvent was evaporated in vacuo an the residue was chromatographed on silica gel eluting with a mixture of hexane and ethyl acetate (1:2) to give methyl 3-acetamido-4-(5-methoxycarbonyl-1-pentynyl)-benzoate (1.15 g) as colorless crystals.

Aufarbeitung

  1. customThe solvent was evaporated in vacuo an the residue
  2. customwas chromatographed on silica gel eluting with a mixture of hexane and ethyl acetate (1:2)

Quellen und Nachweise

ORD-Eintrag
ord-28b80c2cdc5a4419813945f88a1a28ba
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06358992B1

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