Hydrochloric Acid → N-Benzoyl-3-phenylisoserine, (2R,3S)-

HRID 487371

Reaktionsgleichung

Reaktionsgleichung von HRID 487371
[C:1]1([C@@H:7]([C@H:9]([C:11]([OH:13])=[O:12])[OH:10])[NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.C(=O)(O)[O-].[Na+].[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O.ClCCl>[C:20]([NH:8][C@@H:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C@H:9]([C:11]([OH:13])=[O:12])[OH:10])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric Acid2×HCID 7412Benzoyl chlorideHCID 516892Sodium BicarbonateHCID 70207633-Phenylisoserine, (2R,3S)-

Produkt 1

HCID 2762289N-Benzoyl-3-phenylisoserine, (2R,3S)-Ausbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of compound 5.HCl (219 mg, 1.00 mmol) in water (10 mL) containing sodium bicarbonate (500 mg, 5.95 mmol) was added a solution of benzoyl chloride (0.14 mL, 1.20 mmol) in dichloromethane (5.0 mL). The mixture was vigorously stirred for 16 h at room temperature. The reaction mixture was acidified with 0.1N HCl and the crude product was extracted with ethyl acetate (40 mL×3). The combined organic extracts were dried over anhydrous magnesium sulfate and concentrated in vacuo to dryness. The residue was purified on a short silica gel column using chloroform/methanol (2/1) as the eluant to give N-benzoyl-(2R,3S)-3-phenylisoserine (6) (205 mg, 72%) as a white solid.

Aufarbeitung

  1. extractionthe crude product was extracted with ethyl acetate (40 mL×3)
  2. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo to dryness
  4. customThe residue was purified on a short silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-01d7f9b6a7c348acb29c19cf0c535ecb
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05294737

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