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

HRID 9095

Reaction equation

HRID 9095 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

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%).

Workup

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

Sources & evidence

ORD record
ord-7b8cb11dcdcf4486a625205a9d01af52
Source dataset
uspto-grants-2006_08
Patent number
US07091223B2

Linked notes

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