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4-Chlorobenzenesulfonyl chloride → tert-butyl (2R)-2-{[(4-chlorophenyl)sulfonyl]amino}propanoate

HRID 1364331
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1364331
Cl.[C:2]([O:6][C:7](=[O:11])[C@@H:8]([CH3:10])[NH2:9])([CH3:5])([CH3:4])[CH3:3].C(N(CC)CC)C.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>C(Cl)Cl>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([NH:9][C@H:8]([CH3:10])[C:7]([O:6][C:2]([CH3:5])([CH3:4])[CH3:3])=[O:11])(=[O:28])=[O:27])=[CH:22][CH:21]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 16211919D-Alanine tert-butyl ester hydrochloride

Produkt 1

HCID 66934865tert-butyl (2R)-2-{[(4-chlorophenyl)sulfonyl]amino}propanoateAusbeute 88,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To D-alanine tert-butyl ester hydrochloride (1 g) in methylene chloride (35 ml) solution, triethylamine (1.7 ml) and 4-chlorobenzenesulfonyl chloride (1.1 g) were added under ice cooling and the mixture was stirred at room temperature for 2 hours. The methylene chloride was distilled off in vacuo, then the residue was diluted with ethyl acetate. The obtained solution was successively washed with distilled water, saturated potassium hydrogensulfate aqueous solution, and saturated saline, dried over with anhydrous sodium sulfate, then concentrated. The residue was recrystallized from ethyl acetate/hexane to obtain the title compound (1.47 g).

Aufarbeitung

  1. distillationThe methylene chloride was distilled off in vacuo
  2. additionthe residue was diluted with ethyl acetate
  3. washThe obtained solution was successively washed with distilled water, saturated potassium hydrogensulfate aqueous solution, and saturated saline
  4. dry with materialdried over with anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was recrystallized from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-09d51251b496464d82ffe95d032e67d9
Quelldatensatz
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07888348B2

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