Ethyl bromoacetate → Ethyl 2-(3-(2-ethoxy-2-oxoethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate

HRID 554891Notes

Reaction equation

[CH3:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:16][CH2:15][NH:14][C:13]2=[O:17])[S:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][N:14]1[CH2:15][CH2:16][N:12]([C:4]2[S:5][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:2]([CH3:1])[N:3]=2)[C:13]1=[O:17])[CH3:24]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate (2.00 g, 7.83 mmol), ethyl bromoacetate (1.30 mL, 11.75 mmol) and potassium carbonate (1.62 g, 11.75 mmol) in N,N-dimethylformamide (20 mL) was stirred at 80° C. for 2 h. The reaction mixture was allowed to cool to ambient temperature, and then partitioned between ethyl acetate (75 mL) and water (50 mL). The aqueous layer was extracted with ethyl acetate (75 mL), and the combined organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was triturated with ethyl acetate in hexanes to afford the title compound as a colorless solid (2.03 g, 76%): 1H NMR (300 MHz, CDCl3) δ 4.33-4.13 (m, 6H), 4.09 (s, 2H), 3.76-3.69 (m, 2H), 2.62 (s, 3H), 1.37-1.26 (m, 6H); MS (ES+) m/z 342.3 (M+1).

Workup

temperatureto cool to ambient temperature
custompartitioned between ethyl acetate (75 mL) and water (50 mL)
extractionThe aqueous layer was extracted with ethyl acetate (75 mL)
dry with materialthe combined organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was triturated with ethyl acetate in hexanes

Sources & evidence

ORD record: ord-726f92ba599c463f8263de620c49ae94
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08049016B2

Reaction notes

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