[S:1](Cl)(Cl)=[O:2].N1C=CC=CC=1.[C:11]([O:15][C:16](=[O:29])[NH:17][C:18]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Br:28])[N:23]=1)([CH3:21])[CH2:19][OH:20])([CH3:14])([CH3:13])[CH3:12].Cl>C(Cl)Cl>[C:11]([O:15][C:16]([N:17]1[C:18]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Br:28])[N:23]=2)([CH3:21])[CH2:19][O:20][S:1]1=[O:2])=[O:29])([CH3:12])([CH3:13])[CH3:14]
To an at 0° C. precooled solution of thionyl chloride (3.42 ml, 5.57 g, 46.8 mmol) in pyridine (9.46 ml, 9.25 g, 117.0 mmol) was added dropwise a solution of [1-(6-bromo-pyridin-2-yl)-2-hydroxy-1-methyl-ethyl]-carbamic acid tert-butyl ester (see Example 1 step d), 7.75 g, 23.4 mmol) in DCM (230 ml). The reaction mixture was allowed to stir for 1 h at rt, then 0.5 N aq. HCl and DCM were added, the phases were separated and the aq. phase was twice reextracted with DCM. The combined org. phases were washed with brine, dried over Na2SO4, filtered and concentrated to leave the title compound (mixture of diastereomers) as an orange solid. HPLC RtH4=1.16, 1.20 min (diastereomers); ESIMS: 377, 379 [(M+H)+].
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