D-Phenylalanine → 3-(2-Bromophenyl)propionic acid

HRID 266035

Reaktionsgleichung

Reaktionsgleichung von HRID 266035
N([O-])=O.[Na+].N[C@@H:6]([C:14]([OH:16])=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Br-:17].[K+]>S(=O)(=O)(O)O>[CH:12]1[CH:13]=[C:8]([CH2:7][CH2:6][C:14]([OH:16])=[O:15])[C:9]([Br:17])=[CH:10][CH:11]=1

Komponenten

5

Edukt 3

HCID 71567D-PhenylalanineHCID 253877Potassium BromideHCID 23668193Sodium Nitrite

Produkt 1

HCID 3160103-(2-Bromophenyl)propionic acidAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Sodium nitrite (10.3 g, 280 mmol) was added to a solution of D-phenylalanine (30.0 g, 181 mmol) and potassium bromide (73.5 g) in sulfuric acid (2.5N, 365 ml) over a period of one hour while maintaining the temperature of the reaction mixture at 0° C. The mixture was stirred for an additional hour at 0° C. and then for one hour at room temperature. The reaction solution was extracted with ether, the ether was back extracted with water, and the ether layer was dried over sodium sulfate. Ether was removed in vacuo, and distillation of the oily residue afforded 25.7 g of (R)-2-bromo-3-benzenepropanoic acid; b.p. 141° C. (0.55 mm of Hg); [α]D =+14.5° (c=2.4, chloroform).

Aufarbeitung

  1. extractionThe reaction solution was extracted with ether
  2. extractionthe ether was back extracted with water
  3. dry with materialthe ether layer was dried over sodium sulfate
  4. customEther was removed in vacuo, and distillation of the oily residue

Quellen und Nachweise

ORD-Eintrag
ord-a9c7661f29dc43ce8ac5440c0f49aeec
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05650408

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