Trifluoroacetic acid → N-benzyl-O-benzyl-D-serinamide

HRID 534678

Reaktionsgleichung

Reaktionsgleichung von HRID 534678
[CH2:1]([NH:8][C:9](=[O:28])[C@@H:10]([CH2:19][O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[NH:11]C(OC(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH2:1]([NH:8][C:9](=[O:28])[C@@H:10]([CH2:19][O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[NH2:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 7216909N-benzyl-O-benzyl-N2-Boc-D-serinamide

Produkt 1

HCID 67082833N-benzyl-O-benzyl-D-serinamideAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a solution of N-benzyl-O-benzyl-N2-Boc-D-serinamide (3 g) and dichloromethane (15 mL), trifluoroacetic acid (15 mL) was added. The solution was stirred for 2 hours at 40° C. for completion of reaction. The solution was concentrated under vacuum to remove solvents and subsequently water was added. The aqueous layer was basified to pH 8-10 with 5% sodium hydroxide. The aqueous layer was extracted with ethyl acetate and the combined organic layer was washed with brine solution. Organic layer was concentrated under vacuum to obtain an oily residue solidify by n-Hexane to give 1.55 g of N-benzyl-O-benzyl-D-serinamide.

Aufarbeitung

  1. concentrationThe solution was concentrated under vacuum
  2. customto remove solvents and subsequently water
  3. additionwas added
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washthe combined organic layer was washed with brine solution
  6. concentrationOrganic layer was concentrated under vacuum
  7. customto obtain an oily residue solidify by n-Hexane

Quellen und Nachweise

ORD-Eintrag
ord-637b96a137da4747ae3a5d48b80551ca
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853439B2

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