2,5-Dimethyl-3-furoyl Chloride → (S)-2,5-Dimethyl-furan-3-carboxylic acid (1-{4-[3-(4-ethoxy-phenoxy)-azetidin-1-yl]-phenyl}-ethyl)-amide
Reaction equation
[CH3:1][C:2]1[O:3][C:4]([CH3:10])=[CH:5][C:6]=1[C:7](Cl)=[O:8].[CH2:11]([O:13][C:14]1[CH:33]=[CH:32][C:17]([O:18][CH:19]2[CH2:22][N:21]([C:23]3[CH:28]=[CH:27][C:26]([C@@H:29]([NH2:31])[CH3:30])=[CH:25][CH:24]=3)[CH2:20]2)=[CH:16][CH:15]=1)[CH3:12]>C(Cl)Cl>[CH2:11]([O:13][C:14]1[CH:33]=[CH:32][C:17]([O:18][CH:19]2[CH2:20][N:21]([C:23]3[CH:28]=[CH:27][C:26]([C@@H:29]([NH:31][C:7]([C:6]4[CH:5]=[C:4]([CH3:10])[O:3][C:2]=4[CH3:1])=[O:8])[CH3:30])=[CH:25][CH:24]=3)[CH2:22]2)=[CH:16][CH:15]=1)[CH3:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To 0.015 g (0.10 mmol) 2,5-dimethyl-furan-3-carbonyl chloride in 1 mL DCM is added a mixture of 0.031 g (0.10 mmol) (S)-1-{4-[3-(4-ethoxy-phenoxy)-azetidin-1-yl]-phenyl}-ethylamine (X.1) and 0.010 g (0.10 mmol) TEA in 0.5 mL DCM. The mixture is stirred for 12 h at rt. The solvent is removed in vacuo and the residue is purified by HPLC to yield the desired product.