[CH2:1]([NH:8][CH2:9][C@H:10]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[Cl:21][CH2:22][C:23](Cl)=[O:24]>C(Cl)Cl>[CH2:1]([N:8]([CH2:9][C@H:10]([C:12]1[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=1)[OH:11])[C:23](=[O:24])[CH2:22][Cl:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Dissolve (1S)-2-(benzylamino)-1-(4-fluorophenyl)ethanol (1215 g, 4.96 mol) in 12.15 L DCM and cool the mixture to 0° C. Add NaOH (1M in H2O, 5.46 L, 5.46 mol) dropwise over 30 min. Stir the mixture vigorously for 10 min while maintaining it at 0-3° C.; then add a solution of chloroacetyl chloride (616.5 g, 5.46 mol) in 4.86 L of DCM dropwise over 1 h keeping the temperature below 6° C. Stir the mixture for 1 h at 0° C.; separate the layers; and extract the aqueous phase with DCM (1×2 L). Combine the organic layer and extracts; wash them with 10% hydrochloric acid (1.5 L), water (1.5 L) and 1M NaOH (1 L). Dry over Na2SO4 and filter. Collect the filtrate and remove the solvent under reduced pressure to provide the title compound as a colorless oil (1440 g, 90%). MS (m/z): 322 (M+1).
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