Sulfuric Acid → HCID 67462821, Verbindung

HRID 915750Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 915750
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@@H:19]([C:29]([OH:31])=[O:30])[CH2:20][O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(OC[CH2:37][CH2:38][CH3:39])(=O)C.S(=O)(=O)(O)O.Cl[CH2:46]Cl>>[C:38]([O:30][C:29](=[O:31])[C@@H:19]([CH2:20][O:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[NH:18][C:16]([O:15][CH2:14][CH:12]1[C:13]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:17])([CH3:37])([CH3:39])[CH3:46]

Komponenten

5

Edukt 4

HCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 31272Butyl AcetateHCID 7019719Fmoc-D-Ser(Bzl)-OH

Produkt 1

HCID 67462821HCID 67462821, VerbindungAusbeute 77 %

Versuchsvorschrift

N-[(9H-Fluoren-9-yl)methoxycarbonyl]-O-(benzyl)-D-serine (0.710 g, 1.70 mmole) in dichloromethane (8 mL) was treated with 1-butyl acetate (3 mL) and concentrated sulfuric acid (40 μL) in a sealed flask at 0° C. Upon completion (TLC), the reaction was quenched with of dichloromethane (10 mL) and saturated aqueous potassium bicarbonate (15 mL). The organic layer was washed with distilled water, and evaporated. The resulting residue was purified by flash column chromatography (98:2 dichloromethane/methanol) to yield the title compound as a colorless oil (0.292 g, 77%);

Aufarbeitung

  1. customUpon completion (TLC), the reaction was quenched with of dichloromethane (10 mL) and saturated aqueous potassium bicarbonate (15 mL)
  2. washThe organic layer was washed with distilled water
  3. customevaporated
  4. customThe resulting residue was purified by flash column chromatography (98:2 dichloromethane/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-ae480f33f6ff4297aab2e326c73e53a7
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07268125B2

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