Ethyl 2-((tert-butoxycarbonyl)amino)-4-(hydroxymethyl)thiophene-3-carboxylate → HCID 86596546, Verbindung

HRID 1244156Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1244156
[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH2:11][OH:12])=[CH:9][S:8][C:7]=1[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[O:5])[CH3:2]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH:11]=[O:12])=[CH:9][S:8][C:7]=1[NH:13][C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])=[O:5])[CH3:2]

Komponenten

4

Edukt 1

HCID 57354245Ethyl 2-((tert-butoxycarbonyl)amino)-4-(hydroxymethyl)thiophene-3-carboxylate

Produkt 1

HCID 86596546HCID 86596546, VerbindungAusbeute 95,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418406HCID 178418406, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-t-Butoxycarbonylamino-4-hydroxymethyl-thiophene-3-carboxylic acid ethyl ester (2.83 g, 9.44 mmol) was dissolved in anhydrous CH2Cl2 (165 mL) and treated with manganese dioxide (16.41 g, 188.70 mmol). It was stirred at room temperature for 5 hr then it was filtered through a pad of Celite. The Celite was washed with copious amounts of acetone. The filtrate was concentrated in vacuo to give title compound (2.69 g, 95%). MS m/e (CI) 300.0 (M+H)+; 1H NMR (300 MHz, CDCl3): δ ppm 1.42 (t, 3H), 1.55 (s, 9H), 4.43 (q, 2H), 7.59 (s, 1H), 10.30 (s, 1H), 10.34 (s, 1H).

Aufarbeitung

  1. filtrationit was filtered through a pad of Celite
  2. washThe Celite was washed with copious amounts of acetone
  3. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9dba245dee4646d4bc404fe3a40dee59
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07119205B2

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