Sulfuric Acid → HCID 67462821, Verbindung

HRID 1243296Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1243296
[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(O[C:36]([CH3:39])([CH3:38])[CH3:37])(=O)C.S(=O)(=O)(O)O>ClCCl>[C:36]([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])([CH3:39])([CH3:38])[CH3:37]

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 10908tert-Butyl acetateHCID 7019719Fmoc-D-Ser(Bzl)-OH

Produkt 1

HCID 67462821HCID 67462821, VerbindungAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

N-[(9H-Fluoren-9-yl)methoxycarbonyl]-O-(benzyl)-D-serine (0.710 g, 1.70 mmole) in dichloromethane (8 mL) was treated with t-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%); 1H NMR (CDCl3) δ 1.44 (s, 9H); 3.68 (dd, J=2.9 Hz, J=9.3 Hz, 1H); 3.87 (dd, J=2.9 Hz, J=9.3 Hz, 1H); 4.22 (t, J=7.1 Hz, 1H); 4.30–4.60 (m, 5H); 5.64–5.67 (m, 1H); 7.25–7.39 (m, 9H); 7.58–7.61 (m, 2H); 7.73–7.76 (m, 2H).

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-39edafe9921e4892a336a15ccd0b7fb0
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07119083B2

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