Cl.[CH3:2][N:3]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])=[CH:11][CH:10]=1)[CH2:4][C:5]([OH:7])=[O:6].C1N=CN(C(N2C=NC=C2)=O)C=1.[CH2:32](O)[CH:33]=[CH2:34]>CC#N.CCOC(C)=O>[CH3:2][N:3]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])=[CH:11][CH:10]=1)[CH2:4][C:5]([O:7][CH2:34][CH:33]=[CH2:32])=[O:6]
A mixture of 2-(methyl(4-(methylsulfonamido)benzyl)amino)acetic acid hydrochloride (1.054 g, 3.41 mmol), CDI (1.107 g, 6.83 mmol), and TEA (0.952 ml, 6.83 mmol) in CH3CN (80 ml) was heated at 75° C. for 3 hours. The solvent was evaporated; the residue was dissolved in prop-2-en-1-ol (30 ml, 439 mmol) and heated at 75° C. for 1 hour. The mixture was diluted with EtOAc and washed several times with NH4Cl sat. sol. The organic phase was dried over Na2SO4, the solvent was removed, and the residue was filtered on SCX cartridge (DCM/MeOH 1/1; conc.aq.NH4OH/MeOH 1/9). The basic fraction was evaporated to dryness to give allyl 2-(methyl(4-(methylsulfonamido)benzyl)-amino)acetate as a brown oil (0.942 g, 3.02 mmol, 88% yield, MS/ESI+ 313.2 [MH]+).
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