N-(tert-butoxycarbonyl)glycine → HCID 68187780, compound

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Reaction Steps

A flask was charged with N-{[(1,1-dimethylethyl)oxy]carbonyl}glycine (72.4 mg, 0.413 mmol) and HATU (170 mg, 0.448 mmol) then filled with N,N-dimethylformamide (DMF) (2 mL). DIPEA (0.180 mL, 1.033 mmol) was added and the resulting pale yellow solution was stirred for 5 min. 1-Methylethyl {(2S,4R)-1-acetyl-6-[(hydroxyamino)(imino)methyl]-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl}carbamate (for a preparation, see Intermediate 56) (120 mg, 0.344 mmol) in N,N-dimethylformamide (DMF) (2 mL) was then added via syringe and the resulting mixture was stirred at room temperature for 1 h. The mixture was then stirred at 100° C. under nitrogen for 3.5 h then cooled to room temperature and dissolved in AcOEt. The organic phase was washed with water. The aqueous phase was extracted with AcOEt. The combined organic phases were washed three times with water then brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue by SP4 on a 10 G silica cartridge (gradient 23 to 63% AcOEt in Hexanes) gave 1-methylethyl((2S,4R)-1-acetyl-6-{5-[({[(1,1-dimethylethyl)oxy]carbonyl}amino)methyl]-1,2,4-oxadiazol-3-yl}-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl)carbamate (132 mg, 0.271 mmol, 79% yield) as a white foam. LCMS (method A): Retention time 1.07 min, [M−H]−=486.23

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