Hydrochloric Acid → HCID 178427600, compound

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Reaction Steps

To a solution of thiazole (2.5 g, 29 mmol) in THF (25 mL) at −78° C. is added n-BuLi (1.6 M in hexane, 19 mL) dropwise. The mixture is stirred for 30 minutes. Then a solution of Boc-Arg(Tos)-N(Me)OMe, from Example 1, (1.7 g, 3.6 mmol) in THF (50 mL) is added to the lithiothiazole mixture at —78° C. The solution is stirred for 2 hours. 1M HCl (30 mL) is added to the reaction mixture and warmed to room temperature. The mixture is extracted with EtOAc (100 mL). The organic layer is washed with sat. NaCl (30 mL), dried over MgSO4, filtered and evaporated. The crude oily residue is purified by flash column over SiO2 (50% EtOAc in CH2Cl2) to give Boc-Arg(Tos)-Thiazole, shown above, (1.5 g, 84% yield) as a powder. DCI-MS (M+H)+=496

Provenance & Evidence