C[O-].[Na+].[CH3:4][C:5]([CH3:9])([CH3:8])[CH2:6][SH:7].[C:10]([O:14][C:15]([NH:17][CH2:18][C:19]1[CH:20]=[N:21][C:22]([CH2:25]Cl)=[CH:23][CH:24]=1)=[O:16])([CH3:13])([CH3:12])[CH3:11]>CO.O.C(OCC)(=O)C>[C:10]([O:14][C:15]([NH:17][CH2:18][C:19]1[CH:20]=[N:21][C:22]([CH2:25][S:7][CH2:6][C:5]([CH3:9])([CH3:8])[CH3:4])=[CH:23][CH:24]=1)=[O:16])([CH3:13])([CH3:12])[CH3:11]Under a nitrogen atmosphere, add sodium methoxide (630 mg, 3.51 mmol, 30% w/w in methanol) to a stirring mixture of 2,2-dimethyl-propane-1-thiol (365 mg, 3.51 mmol) and methanol (10 mL) at room temperature and stir for 30 min. Add 3-(tert-butoxycarbonylamino-methyl)-6-chloromethyl-pyridine (450 mg, 1.76 mmol) in methanol (5 mL) and stir the mixture for 2 h. Dilute the mixture with water and ethyl acetate. Separate the layers and extract the aqueous layer with ethyl acetate. Wash the combined organic extracts with water and brine. Dry the organic phase over Na2SO4, filter, and concentrate in vacuo to obtain the desired intermediate suitable for use without additional purification. MS (APCI+) m/z: 325 (M+H)+.
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