p-Toluenesulfonic acid → (R)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamate

HRID 1476258

Reaktionsgleichung

Reaktionsgleichung von HRID 1476258
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:17][OH:18])[CH2:13][C:14]([OH:16])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[O:16]=[C:14]1[O:18][CH2:17][C@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:13]1

Komponenten

4

Edukt 2

HCID 6101p-Toluenesulfonic acidHCID 13340758(R)-3-(((benzyloxy)carbonyl)amino)-4-hydroxybutanoic acid2×

Produkt 1

HCID 697924(R)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamateAusbeute 88,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

(R)-3-(Benzyloxycarbonylamino)-4-hydroxybutanoic acid (INTERMEDIATE 2, 27.7 g, 109.38 mmol) was dissolved in toluene (648 ml). p-Toluenesulfonic acid (367 mg, 2.13 mmol) was added to the solution and the resulting mixture was heated at reflux under Dean-Stark conditions for 3 hours. The reaction mixture was cooled to room temperature and concentrated in vacuo. Diethyl ether (200 ml) was added, and formation of crystals was observed upon standing. The crystals were filtered in vacuo. The mother liquors were concentrated in vacuo and additional diethyl ether (40 ml) was added. More crystals appeared which were filtered in vacuo. Both sets of crystals combined to give the title product (22.8 g, yield: 83%).

Aufarbeitung

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux under Dean-Stark conditions for 3 hours
  3. concentrationconcentrated in vacuo
  4. additionDiethyl ether (200 ml) was added
  5. filtrationThe crystals were filtered in vacuo
  6. concentrationThe mother liquors were concentrated in vacuo and additional diethyl ether (40 ml)
  7. additionwas added
  8. filtrationwere filtered in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8619a08771744286adc9b27137d46e67
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09018381B2

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