Potassium Carbonate → HCID 474117, compound

Reaction equation

[C:1]1([CH2:7][C:8]([C@H:10]2[C@@H:14]([C:15](=O)[CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:13]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)C(=O)[N:11]2[CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])(=O)C.[NH4+].[C:44](=[O:47])([O-])[O-].[K+].[K+]>C(O)(=O)C>[CH2:24]([N:13]1[C:14]2=[C:15]([CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[O:9][C:8]([CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[C:10]2[N:11]([CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:44]1=[O:47])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

Procedure

A solution of (4R-cis)-4,5-bis(phenylacetyl)-1,3-bis(benzyl)-2-imidazolidinone (79 mg, 0.16 mmol) and ammonium acetate (25 mg, 0.32 mmol) in acetic acid (2 ml) was refluxed 18 hours. The solution was neutralized with solid potassium carbonate and partitioned between EtOAc/water. The aqueous phase was washed twice with EtOAc. All organic extracts were combined and dried over MgSO4, then concentrated to a brown oil. Further purification was achieved by preparative TLC (silica gel, 30% EtOAc/hexane) to give the product as a yellow-brown oil, (59 mg, 76% yield). 1HNMR (CDCl3) δ7.10-7.44 (m, 10H), 4.99-5.16 (m, 2H) , 4.17-4.29 (m, 3H), 3.59 (d, 1H), 2.54 (m, 1H), 2.07-2.33 (m, 3H), 1.21-1.50 (m, 6H), 0.84-0.93 (m, 6H). MS: 417 (M+1).