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

HRID 1720585

Reaktionsgleichung

Reaktionsgleichung von HRID 1720585
[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 (0.78g, 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-8fe7910cc3df45098a03339428ce79b0
Quelldatensatz
uspto-grants-1996_04
Patentnummer
US05506242

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