Sodium Chloride → (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-(5-chloropentanamido)propan-2-ylcarbamate

関与物質

反応条件

反応手順

(S)-tert-butyl 1-amino-3-(tert-butyldimethylsilyloxy)propan-2-ylcarbamate (1 g, 3.29 mmol) was taken up in 10 mL of CH2Cl2 and cooled to 0° C. To this was added Et3N (0.731 g, 7.24 mmol), followed by 5-chloro-pentanoyl chloride (0.557 g, 3.62 mmol). The reaction mixture was allowed to warm to rt and stirred for 4 h. Upon completion of the reaction, satd NaCl solution was added. The organic layer was extracted with EA, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by column to give (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-(5-chloropentanamido)propan-2-ylcarbamate (1.2 g, 86%). 1H NMR (CDCl3, 300 MHz) δ 6.31 (s, 1H), 5.04 (d, 1H), 3.65 (m, 3H), 3.53 (m, 2H), 3.40 (m, 2H), 2.18 (t, 2H), 1.78 (m, 4H), 1.43 (s, 9H), 0.88 (s, 9H), 0.0 (s, 6H).

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