Potassium Carbonate → [1-(4-Methoxy-benzyl)-2,5-dioxo-imidazolidin-4-yl]-acetic acid methyl ester

HRID 1985115Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:12])[CH2:4][CH:5]1[C:9](=[O:10])[NH:8][C:7](=[O:11])[NH:6]1.[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Cl)=[CH:17][CH:16]=1.[O-]S([O-])(=O)=O.[Mg+2].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:12])[CH2:4][CH:5]1[C:9](=[O:10])[N:8]([CH2:19][C:18]2[CH:21]=[CH:22][C:15]([O:14][CH3:13])=[CH:16][CH:17]=2)[C:7](=[O:11])[NH:6]1

Participants

Conditions

Temperature: 45 °C

Procedure

A solution of (2,5-dioxo-imidazolidin-4-yl)-acetic acid methyl ester (26.6 g, 0.155 mol) in DMF (500 mL) was treated with 4-methoxybenzyl chloride (26.6 g, 0.170 mol), MgSO4 (18.6 g, 0.154 mol) and then 325 mesh K2CO3 (42.71 g, 0.309 mol) at 0° C. The resultant mixture was warmed to room temperature under N2 and then heated at 45° C. for 4 h. The reaction mixture was filtered, and then aqueous 1N HCl (200 mL) was added to the filtrate. The filtrate was extracted with EtOAc and the organic layer dried (MgSO4). The solvent was removed in vacuo to give 11.43 g crude product which was purified by flash chromatography using a gradient of 3:1 to 1:1 hexanes:acetone to give 9.81 g (22%) [1-(4-methoxy-benzyl)-2,5-dioxo-imidazolidin-4-yl]-acetic acid methyl ester. MS (ES+) Calc'd for C14H17N2O5 (M+1) 293. Found m/z 293 (100%). 1H NMR.

Workup

customat 0° C
filtrationThe reaction mixture was filtered
additionaqueous 1N HCl (200 mL) was added to the filtrate
extractionThe filtrate was extracted with EtOAc
dry with materialthe organic layer dried (MgSO4)
customThe solvent was removed in vacuo
customto give 11.43 g crude product which
customwas purified by flash chromatography

Sources & evidence

ORD record: ord-381203cf48ca4fdd96fdda8bd291c46e
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07544812B2

Reaction notes

Loading…