Hydrochloric Acid → N-benzoyl-L-alanine

HRID 1040262

Reaktionsgleichung

Reaktionsgleichung von HRID 1040262
[OH-].[Na+].[NH2:3][CH:4]([C:6]([OH:8])=[O:7])[CH3:5].[C:9](Cl)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl>O>[C:9]([NH:3][C@H:4]([C:6]([OH:8])=[O:7])[CH3:5])(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 602DL-alanineHCID 7412Benzoyl chlorideHCID 14798Sodium Hydroxide

Produkt 1

HCID 709778N-benzoyl-L-alanineAusbeute 90,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To a solution of sodium hydroxide (8.98 g, 224.49 mmol) in water (112.25 mL), was added at rt DL-Alanine (10 g, 112.25 mmol). The resulting solution was heated at 75° C. and the benzoyl chloride (15.77 g, 112.25 mmol) was slowly added. The reaction was heated for 30 minutes, and cooled down to 0° C. with an ice bath. Conc. HCl was added to adjust the pH to 1, then the white solid was filtrated through a fritted glass funnel and vacuum dried with P2O5 overnight. No purification was needed. This gave N-benzoylalanine (19.6 g, 90.4% yield) as white solid. 1H NMR (DMSO-d6) δ 12.61 (s br, 1H), 8.64 (d, 1H), 7.87-7.85 (m, 2H), 7.52-7.43 (m, 3H), 4.40 (q, 1H), 1.39 (d, 3H).

Aufarbeitung

  1. temperatureThe reaction was heated for 30 minutes
  2. temperaturecooled down to 0° C. with an ice bath
  3. filtrationthe white solid was filtrated through a fritted glass funnel
  4. dry with materialvacuum dried with P2O5 overnight
  5. customNo purification

Quellen und Nachweise

ORD-Eintrag
ord-ad5a7fbc967b47e1be327bab08a1e70a
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552203B2

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