Br[C:2]1[S:3][C:4]([NH:12][CH3:13])=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.[NH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21].CCOP(O)N(C(C)C)C(C)C>O1CCOCC1>[C:20]([O:19][C:18]([NH:17][CH2:16][CH2:15][NH:14][C:2]1[S:3][C:4]([NH:12][CH3:13])=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1)=[O:24])([CH3:23])([CH3:22])[CH3:21]Ethyl 2-bromo-5-methylamino-thiazole-4-carboxylate (546 mg, 2.059 mmol) and tert-butyl N-(2-aminoethyl)carbamate (1.3 g, 8.11 mmol) were combined in anhydrous 1,4-dioxane (15 ml). EDIPA (3 ml, 17.2 mmol) was added and the mixture was heated in a sealed tube for 23 hours at 100° C. The mixture was cooled to room temperature and partitioned between DCM and a saturated solution of sodium bicarbonate. Layers were separated, the aqueous phase was extracted twice with DCM and the combined organic layers were dried over sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by column chromatography (silica, gradient of 30 to 100% ethyl acetate in heptane) to yield 185 mg (0.537 mmol, 26%) MS(ESI) m/z=345.2 [M+1]+.
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