Tetrahydrofuran → Ethyl-2-tert-butoxycarbonyloxyamino-4-methyl-thiazole-5-carboxylate

HRID 458242

Reaktionsgleichung

Reaktionsgleichung von HRID 458242
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([NH2:11])=[N:8][CH:7]=1)=[O:5])[CH3:2].[C:12]([O:16][C:17]([O:19]C(OC(C)(C)C)=O)=[O:18])([CH3:15])([CH3:14])[CH3:13].O1CCC[CH2:28]1>CN(C)C1C=CN=CC=1>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([NH:11][O:19][C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:18])=[N:8][C:7]=1[CH3:28])=[O:5])[CH3:2]

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 90495Di-tert-butyl dicarbonateHCID 3146282-Amino-thiazole-5-carboxylic acid ethyl ester

Produkt 1

HCID 21911455Ethyl-2-tert-butoxycarbonyloxyamino-4-methyl-thiazole-5-carboxylateAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 142844-(Dimethylamino)pyridineKatalysator

Versuchsvorschrift

A suspension of ethyl-2-amino-thiazole-5-carboxylate (972 mg, 6 mmol, B. Plouvler, C. Bailly, R. Houssin, j-P. Henlchart Heterocyles 32(4), 693–701, 1991 and H. J. Becker, J. de Jonge Rec. Trav. Chim, 61, 463, 1942), di-t-butyldicarbonate (1.94 g, 9 mmol) and 4-dimethylaminopyridine (73 mg, 0.6 mmol) in dry tetrahydrofuran (75 mL) was stirred under nitrogen for 24 h. The solvent was evaporated in vacuo. The residue was suspended in ether (50 mL). The solid was washed with ether (10 mL, 3×), and dried in vacuo to obtain the title compound (1.1 g, 70%).

Aufarbeitung

  1. customThe solvent was evaporated in vacuo
  2. washThe solid was washed with ether (10 mL, 3×)
  3. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-15c51b6ac41049f0a078b6f748bbcf3d
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07189854B2

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