p-Bromobenzenesulfonyl chloride → methyl N-[(4-bromophenyl)sulfonyl]-L-valinate

HRID 29280

Reaktionsgleichung

Reaktionsgleichung von HRID 29280
Cl.[CH3:2][O:3][C:4](=[O:10])[C@H:5]([CH:7]([CH3:9])[CH3:8])[NH2:6].[Br:11][C:12]1[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[Br:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([NH:6][C@H:5]([C:4]([O:3][CH3:2])=[O:10])[CH:7]([CH3:9])[CH3:8])(=[O:20])=[O:19])=[CH:14][CH:13]=1

Komponenten

5

Edukt 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 111190Methyl valinate hydrochloride

Produkt 1

HCID 47337186methyl N-[(4-bromophenyl)sulfonyl]-L-valinateAusbeute 101,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To 0.838 g of L-valine methyl ester hydrochloride in 15 mL of dichloromethane, cooled in an ice bath, 1.34 g of 4-bromobenzenesulfonyl chloride was added followed by 2.79 mL of triethylamine. The mixture was stirred at room temperature overnight and then diluted with dichloromethane. The dichloromethane was washed with water and brine, dried over Na2SO4, filtered, and concentrated in vacuo to provide 1.77 g of methyl N-[(4-bromophenyl)sulfonyl]-L-valinate as a colorless solid. Yield ˜100%. m.p. 88-90° C.; MS: 348.2 (M−H)−.

Aufarbeitung

  1. washThe dichloromethane was washed with water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c7aee23be9fa4d6ea3058bed23397285
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07420001B2

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