Benzenesulfonyl chloride → N-benzenesulfonylglycyl-L-proline benzylester

HRID 1073990

Reaktionsgleichung

Reaktionsgleichung von HRID 1073990
Cl.[CH2:2]([O:9][C:10](=[O:20])[C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16](=[O:19])[CH2:17][NH2:18])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:28]1([S:34](Cl)(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(Cl)Cl>[CH2:2]([O:9][C:10](=[O:20])[C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16](=[O:19])[CH2:17][NH:18][S:34]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=[O:36])=[O:35])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 13068147glycyl-L-proline benzylester hydrochloride

Produkt 1

HCID 14858890N-benzenesulfonylglycyl-L-proline benzylesterAusbeute 94,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

Glycyl-L-proline benzylester hydrochloride (1.49 g, 5 mmole) was dissolved in methylene chloride (30 ml), and triethylamine (1.11 g, 11 mmole) was added thereto at -30° C., and then methylene chloride (10 ml) solution of benzenesulfonylchloride (0.86 g, 5 mmole) was added dropwise. The mixture was stirred for 1 hour at less than 0° C, and then for 5 hours at room temperature, and methylene chloride (60 ml) was added. The mixture thus obtained was washed with 5% aqueous sodium bicarbonate (100 ml, twice), 1N aqueous hydrochloric acid (100 ml, twice) and water (100 ml) in the order given, and dried over anhydrous magnesium sulfate. The solvent was distilled under reduced pressure to give N-benzenesulfonylglycyl-L-proline benzylester (yield: 1.91 g, 94.9%).

Aufarbeitung

  1. waitfor 5 hours at room temperature
  2. customThe mixture thus obtained
  3. washwas washed with 5% aqueous sodium bicarbonate (100 ml
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-958a0c1fa24948f081e45962559c8a3e
Quelldatensatz
uspto-grants-1990_11
Patentnummer
US04971993

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