Triethylamine → 5-(3-Methanesulfonylamino-propyl)-furan-2-carboxylic acid methyl ester

HRID 1699090Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1699090
Cl.[CH3:2][O:3][C:4]([C:6]1[O:7][C:8]([CH2:11][CH2:12][CH2:13][NH2:14])=[CH:9][CH:10]=1)=[O:5].C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C(Cl)Cl>[CH3:2][O:3][C:4]([C:6]1[O:7][C:8]([CH2:11][CH2:12][CH2:13][NH:14][S:23]([CH3:22])(=[O:25])=[O:24])=[CH:9][CH:10]=1)=[O:5]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 692922505-(3-Amino-propyl)-furan-2-carboxylic acid methyl ester hydrochloride salt

Produkt 1

HCID 537273525-(3-Methanesulfonylamino-propyl)-furan-2-carboxylic acid methyl esterAusbeute 87,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 5-(3-amino-propyl)-furan-2-carboxylic acid methyl ester hydrochloride salt (see Preparation DD2) (150 mg, 0.683 mmol), and triethylamine (0.313 mL, 2.25 mmol) in CH2Cl2 (15 mL) at 0° C. was added methanesulfonyl chloride (86 mg, 0.75 mmol). The reaction was stirred at room temperature for 18 h. The organic solution was washed consecutively with dilute HCl, water, saturated NaHCO3, and brine. The organic solution was dried over MgSO4, filtered, and concentrated to provide the title sulfonamide (156 mg). MS 262 (M+1).

Aufarbeitung

  1. washThe organic solution was washed consecutively with dilute HCl, water, saturated NaHCO3, and brine
  2. dry with materialThe organic solution was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-65adc9bc50cb4778b02e8b354cd5ac36
Quelldatensatz
uspto-grants-2002_02
Patentnummer
US06344485B1

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