Sulfuric Acid → HCID 67462821, Verbindung

HRID 1968416Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1968416
[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, Verbindung

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 0.292 g (77%) as a colorless oil; 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)
  5. customto yield 0.292 g (77%) as a colorless oil

Quellen und Nachweise

ORD-Eintrag
ord-8e8e5ed706004eac93efaca41a9a1c38
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426400B2

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