Benzyl bromoacetate → HCID 90001511, compound

Participants

Reaction Steps

DIPEA (0.23 mL, 2.0 eq.) was added to a solution of 18 (0.19 g, 1.0 eq.) in dry acetonitrile (1.5 mL) at 0° C. Benzylbromoacetate (0.11 mL, 1.0 eq.) was added in one portion and the reaction was allowed to warm to room temperature and stir for 18 hrs. A further portion of benzyl bromoacetate (55 μL) was added and the reaction was stirred for a further 2 h. The reaction was diluted with water (20 mL) and extracted into ethyl acetate (3×20 mL). The combined organic phases were washed with water (50 mL) and brine (50 mL) before being dried (MgSO4), filtered and concentrated at reduced pressure to yield give a colourless oil (0.40 g). The crude product was purified by silica column chromatography eluting with 3% methanolic ammonia in DCM to give 0.23 g (79%) of 19 as a colourless oil. 13C NMR (CDCl3) δ 171.3, 156.2, 135.7, 128.6, 128.4, 79.0, 72.3, 70.2, 69.4, 69.2, 66.2, 61.9, 55.2, 54.2, 40.5, 28.5. ESMS (C22H36N2O7) [M+H]+ calc. 441.2601. found 441.2596.

Provenance & Evidence