[CH2:1]([NH:8][C@H:9]([CH3:12])[CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:13][CH2:14][C:15](Cl)=[O:16].O>ClCCl>[CH2:1]([N:8]([C@H:9]([CH3:12])[CH2:10][OH:11])[C:15](=[O:16])[CH2:14][Cl:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1(R)-2-(Benzylamino)propan-1-ol (16.58 g, 100 mmol) was dissolved in dichloromethane (125 mL) and TEA (18.1 mL, 130 mmol) before being cooled to −10° C. in a methanol/ice bath. Chloroacetic acid chloride (8.78 mL, 110 mmol) was added dropwise and the mixture was stirred for 1.5 h at −10° C. A small amount of water was then added to remove the amine. The reaction mixture was poured into a separatory funnel, washed 2×50 mL with dichloromethane, separated, organic layers dried over sodium sulfate, concentrated in vacuo, and purified by flash chromatography to give the title compound.
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