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Friday, 17 July 2015

(2S) -N- tert-butoxycarbonylamino-1-amino-3- [[3-fluoro-4- (4-morpholinyl) phenyl] - acetamido] -2-propanol

Figure CN103483294AD00092


Example 9


(2S) -N- tert-butoxycarbonylamino-1-amino-3- [[3-fluoro-4- (4-morpholinyl) phenyl] - acetamido] -2-propanol (8a) Preparation of The (27?) - # - t-butoxycarbonylamino-1-amino-3 - [[3-fluoro-4- (4-morpholinyl) phenyl] amino] -2-propanol (0.03 mol), two After 100 ml of methyl chloride and triethylamine (0.04 mol) added to the reaction flask, stir, set in an ice bath to cool to 0-5 ° C, was added dropwise acetyl chloride (0. 033 mol), stirred at room temperature for 3 hours The reaction was washed with aqueous NaHC03, washed with saturated aqueous NaCl, the organic layer was dried over anhydrous Na2S04, the solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography (eluent: petroleum ether / ethyl acetate = 1/30 v / v), to give a pale yellow oil in a yield of 85.0%; 



Figure CN103483294AD00092


Che NMR (CDC13,400MHz) 
8: 6. 92 (m, 3H, Ar-H), 
5. 23 (brs, 1H, NHCO) , 
3. 89 (t, J = 4. 4Hz, 4H, 2 X CH20), 
3. 85 (m, 1H, CHO), 
3. 83 (m, 1H, CH2N-Ar), 
3. 59 (d, J = 12Hz, 1H, CH2NAr), 
3. 33 (m, 1H, CH2NC0), 
3. 12 (t, / = 4. 8Hz, 4H, 2 X CH2N), 
3. 04 (m, 1H, CH2NC0), 
1. 89 (s, 3H, CH3), 
1. 43 (s, 9H, CH3). 









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