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

HRID 1020294Notes

Reaction equation

HRID 1020294 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-9bb363f9f6b64eafad8b01262ee02ce8
Source dataset
uspto-grants-2014_05
Patent number
US08716323B2

Reaction notes

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