4-Methoxybenzenesulfonyl chloride → 1-[(4-Methoxyphenyl)sulfonyl]-D-proline

HRID 264290

Reaktionsgleichung

Reaktionsgleichung von HRID 264290
[NH:1]1[CH2:8][CH2:7][CH2:6][C@@H:2]1[C:3]([OH:5])=[O:4].C(N(CC)CC)C.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>C(Cl)Cl>[CH3:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([S:24]([N:1]2[CH2:8][CH2:7][CH2:6][C@@H:2]2[C:3]([OH:5])=[O:4])(=[O:26])=[O:25])=[CH:22][CH:23]=1

Komponenten

5

Edukt 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 8988D-Proline

Produkt 1

HCID 7449021-[(4-Methoxyphenyl)sulfonyl]-D-proline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

(D)-proline (0.78 g, 6.77 mmol) is suspended in methylene chloride (25.0 mL). To this solution is added triethylamine (1.13 mL, 8.12 mmol) and 4-methoxybenzenesulfonyl chloride (1.4 g, 6.77 mmol), and the reaction is stirred at room temperature for two days. The reaction is then diluted with methylene chloride and washed successively with 1N hydrochloric acid, water, and brine. The organic phase is dried (MgSO4), and the solvent is evaporated. The product is purified by silica gel chromatography (10% methanol/ethyl acetate) to give 1-[4-methoxybenzenesulfonyl]-pyrrolidine-2(R)-carboxylic acid.

Aufarbeitung

  1. washwashed successively with 1N hydrochloric acid, water, and brine
  2. dry with materialThe organic phase is dried (MgSO4)
  3. customthe solvent is evaporated
  4. customThe product is purified by silica gel chromatography (10% methanol/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-f54f586025c04cceb28d30155010910e
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05646167

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