Hydrochloric Acid → HCID 11038164, compound

Reaction equation

C(OC(N[CH2:9][P:10]([CH2:15][NH:16][C:17](OC(C)(C)C)=O)(=[O:14])[O:11][CH2:12][CH3:13])=O)(C)(C)C.Cl.[C:25]1([C:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[NH:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(Cl)Cl>[C:33]1([C:31]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[N:32][CH2:9][P:10]([CH2:15][N:16]=[C:17]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:14])[O:11][CH2:12][CH3:13])[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

Procedure

The tert-butoxycarbonyl protective group is removed from the ethyl phosphinate 2 (100 mg; 0.28 mmol) using 3N methanolic hydrochloric acid (30 ml) (check via DC). The reaction solution is evaporated under reduced pressure. Diphenylmethanimine (0.100 ml; 0.60 mmol) is added dropwise to the suspension of the crude product in methylene chloride (20 ml) under an atmosphere of nitrogen. The reaction solution is filtered after being stirred for 16 hours at room temperature. The filtrate is evaporated under reduced pressure. The crude product is taken up in ether, filtered and extracted with water (2×20 ml). The organic phase is dried over Na2SO4 and evaporated under reduced pressure. The diphenylmethylene phosphinate 3 (71 mg, 53% of theory) is obtained after purification on silica gel using column chromatography (ethyl acetate/heptane=1/1).