p-Toluenesulfonic acid → 3,3-Dimethoxy-4-benzyloxycarbonylamino-tetrahydrofuran

HRID 413230Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 413230
CO[CH:3]([O:6][CH3:7])[O:4][CH3:5].[CH2:8]([O:15][C:16]([NH:18][CH:19]1[CH2:23][O:22][CH2:21]C1=O)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CC1C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:7][O:6][C:3]1([O:4][CH3:5])[CH:19]([NH:18][C:16]([O:15][CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[O:17])[CH2:23][O:22][CH2:21]1

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 18523485Benzyl (4-oxotetrahydrofuran-3-yl)carbamate

Produkt 1

HCID 185234863,3-Dimethoxy-4-benzyloxycarbonylamino-tetrahydrofuran

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Trimethylorthoformate (29 ml) was added dropwise to a refluxing solution of 4-benzyloxycarbonylamino-tetrahydrofuran-3-one (18 g, 78 mmol) and PTSA (500 mg) in MeOH (100 ml). After 3 hours, the reaction mixture was filtered and concentrated to afford, after column chromatography, the title compound as a yellow oil, 16.2 g, 76%.

Aufarbeitung

  1. filtrationthe reaction mixture was filtered
  2. concentrationconcentrated
  3. customto afford

Quellen und Nachweise

ORD-Eintrag
ord-3d9832a0659e4d9e8f4e2e1c7e6193da
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06566373B2

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