Ethyl Acetate → HCID 91176746, compound

Reaction equation

[OH:1][CH2:2][CH2:3][S:4]([CH2:7][CH2:8][O:9][C:10]([O:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)=[O:11])(=[O:6])=[O:5].[NH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27]([C:40]1[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[C:48](OCC)(=[O:50])C>>[N+:19]([C:16]1[CH:17]=[CH:18][C:13]([O:12][C:10]([O:9][CH2:8][CH2:7][S:4]([CH2:3][CH2:2][O:1][C:48](=[O:50])[NH:22][CH2:23][CH2:24][CH2:25][NH:26][C:27]([C:40]2[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)(=[O:6])=[O:5])=[O:11])=[CH:14][CH:15]=1)([O-:21])=[O:20]

Participants

Reactant 3

HCID 8857Ethyl Acetate

HCID 13871405HCID 13871405, compound

HCID 22890091HCID 22890091, compound

Product 1

HCID 91176746HCID 91176746, compoundYield 35%

Procedure

A solution of 18 (0.68 g, 2.13 mmol) and (3-aminopropyl)[(4-methoxyphenyl)diphenylmethyl]amine (0.89 g, 2.56 mmol) was stirred at 40° C. for 30 min. p-nitrophenyl chlorofornate (0.62 g, 3.08 mmol) was added and stirring was continued for an additional 2 h. The solution was diluted with ethyl acetate (350 ml), washed with water (300 ml) and then dried over sodium sulfate and evaporated. The residue was purified by silica gel chromatography eluting with a gradient of 40-100% ethyl acetate in hexane. The pure product fractions were evaporated affording a foam: 351 mg of 20 (35%) yield; 1H NMR (DMSO-d6) δ 8.32 (2H, d, J=9.2 Hz, aromatic), 7.56 (1H, d, J=9.2 Hz, aromatic), 7.37 (4H, d, J=7.4 Hz, aromatic), 7.29-7.15 (8H, m, aromatic), 6.83 (2H, d, J=8.9 Hz, aromatic), 4.61 (2H, t, J=5.5 Hz, CH2), 4.29 (2H, t, J=6.0 Hz, CH2), 3.71 (3H, s, methoxy), 3.67 (2H, t, J=5.7 Hz, CH2), 3.51 (2H, t, J=5.8 Hz, CH2), 3.07 (2H, m, CH2), 1.93 (2H, m, CH2), 1.59 (2H, m, CH2).