Methyl iodide → Methyl 11-(benzyloxycarbonylamino)undecanoate

A suspension of 18 (2.91 g, 8.68 mmol), Cs2CO3 (4.25 g, 13.02 mmol) and DMF (anhydrous, 40 mL) was stirred at room temperature for 1.5 h. To the mixture was then added methyl iodide (0.83 mL, 13.02 mmol), and stifling was continued for an additional 3 h at the ambient temperature. The mixture was then partitioned between water (150 mL) and dichloromethane (150 mL), aqueous layer was separated and washed with dichloromethane (3×300 mL). Organics were combined, dried over anhydrous Na2SO4, concentrated and further dried under high vacuum overnight to afford the desired methyl ester 19 (3.41 g, quant yield): 1H NMR (500 MHz, CDCl3) δ 1.26 (m, 12H), 1.47 (m, 2H), 1.52 (m, 2H), 2.28 (m, 2H), 3.16 (m, 2H), 3.66 (s, 3H), 5.10 (s, 2H), 7.32 (m, 5H); m/z (ESI) 350 [M+H]+.

1. customThe mixture was then partitioned between water (150 mL) and dichloromethane (150 mL), aqueous layer
2. customwas separated
3. washwashed with dichloromethane (3×300 mL)
4. dry with materialdried over anhydrous Na2SO4
5. concentrationconcentrated
6. customfurther dried under high vacuum overnight

ORD record

ord-7c9e43731f714e76b77e99af849ac9e1

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08324218B2