Diisopropylethylamine → Tert-butyl 5-(methylcarbamoyl)thiazol-2-ylcarbamate

HRID 1874007Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1874007
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][C:11]([C:14]([OH:16])=O)=[CH:12][N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.O[N:19]1[C:23]2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.Cl.CN>C(#N)C>[CH3:23][NH:19][C:14]([C:11]1[S:10][C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[N:13][CH:12]=1)=[O:16]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 6364545Methylamine hydrochlorideHCID 222714422-N-Boc-Amino-Thiazole-5-Carboxylic Acid

Produkt 1

HCID 86649520Tert-butyl 5-(methylcarbamoyl)thiazol-2-ylcarbamateAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a heterogeneous mixture of 2-(tert-butoxycarbonylamino)thiazole-5-carboxylic acid (1.0 g, 4.1 mmol), 1-hydroxybenzotriazole hydrate (0.63 g, 4.1 mmol), N,N-diisopropylethylamine (4.3 mL, 24 mmol), methylamine hydrochloride (0.83 g, 12 mmol) in anhydrous acetonitrile (20 mL), was added WSCDI (2.4 g, 12 mmol) at room temperature under a nitrogen atmosphere and stirred at room temperature overnight. The reaction mixture was concentrated in vacuo. To the residue was added saturated aqueous sodium bicarbonate solution (20 mL), ethyl acetate (6 mL), and heptane (2 mL). The solid that separates out was filtered, washed with water (2×2 mL) and diethyl ether (2×4 mL), and dried to give tert-butyl 5-(methylcarbamoyl)thiazol-2-ylcarbamate (0.77 g, 73% yield) as a white solid. MS found: (M+H)+=258; 1H NMR (400 MHz, methanol-d4) δ ppm 7.83 (s, 1H), 2.87 (s, 3H), 1.55 (s, 9H).

Aufarbeitung

  1. additionwas added WSCDI (2.4 g, 12 mmol) at room temperature under a nitrogen atmosphere
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additionTo the residue was added saturated aqueous sodium bicarbonate solution (20 mL), ethyl acetate (6 mL), and heptane (2 mL)
  4. filtrationThe solid that separates out was filtered
  5. washwashed with water (2×2 mL) and diethyl ether (2×4 mL)
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-4b75c05436cc4bc0a166d7589795cc22
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304539B2

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