Bromide ion → (S)-2-(4-bromobenzyl)amino-3-methylbutyric acid

HRID 12593

Reaktionsgleichung

Reaktionsgleichung von HRID 12593
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4].C(N([CH:15]([CH3:17])[CH3:16])CC)(C)C.[Br-:18].[OH-].[Na+]>CN(C=O)C.O.C1(C)C=CC=CC=1>[Br:18][C:16]1[CH:15]=[CH:17][C:3]([CH2:4][NH:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4])=[CH:2][CH:6]=1

Komponenten

8

Edukt 4

HCID 259Bromide ionHCID 6287L-ValineHCID 14798Sodium HydroxideHCID 81531Diisopropylethylamine

Produkt 1

HCID 11673643(S)-2-(4-bromobenzyl)amino-3-methylbutyric acidAusbeute 153,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
22.5 °C

Versuchsvorschrift

52 mL (0.21 mol) of N,O-bistrimethylsilylacetamide is added under nitrogen atmosphere to a mixture made up of 23.5 g (0.20 mol) of L-valine and 38.5 mL (0.22 mol) of diisopropylethylamine in 12.5 mL of DMF. After 1 h at 80° C. the suspension changes to a clear solution. Then, in portions and controlling exothermy, 50 g (0.20 mol) of 4-bromobenzylo bromide is added and left to react at 80° C. for 2 h. The mixture is cooled to 20-25° C., 250 mL of toluene and a solution made up of 250 mL of water and 80 mL of NaOH 40% are added. The resulting aqueous phase is washed twice with 100 mL of AcOEt, the remains of solvent distilled and taken to pH 6-7 with HCl 3N. The solid obtained is filtered with 250 mL of IPA to give 43.9 g (76.5%) of N-(4-bromobenzyl)-L-valine.

Aufarbeitung

  1. additionis added
  2. waitleft
  3. customto react at 80° C. for 2 h
  4. additionare added
  5. washThe resulting aqueous phase is washed twice with 100 mL of AcOEt
  6. distillationthe remains of solvent distilled
  7. customThe solid obtained
  8. filtrationis filtered with 250 mL of IPA

Quellen und Nachweise

ORD-Eintrag
ord-145a239c04c24a43b4d3485f843fcd6d
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728021B2

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