tert-Butyl bromoacetate → HCID 15319065, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of compound (18) (6.84 g, 15.53 mmol) in dry MeCN (150 ml) were added N,N′-diisopropylethyl amine (13.52 ml, 10.03 g, 77.63 mmol) and tert-butyl bromoacetate (4.82 ml, 6.36 g, 32.61 mmol). The reaction mixture was slowly heated to 60° C., and stirred for 10 hours. The solvent was evaporated under reduced pressure, and the residue was dissolved in a Na2CO3 solution (100 ml). The aqueous layer was extracted with CH2Cl2 (3×100 ml), and the combined extract was washed with brine and dried over MgSO4 to obtain a concentrated white oil. The oil was recrystallized from Et2O to provide compound (19) as a white solid (9.55 g, 92% yield). 1H NMR (500 MHz, CDCl3): δ 7.26-7.19 (m, 10H), 5.04 (s, 4H), 3.34-3.05 (m, 12H), 2.9-2.6 (m, 8H), 1.35 (s, 18H); 13C NMR (125 MHz, CDCl3): δ 170.4, 156.3, 136.7, 128.3, 127.8, 127.7, 80.8, 66.8, 55.8, 54.2, 46.9, 46.5, 28.1; HRMS (FAB) calculated for C36H53N4O8: 669.3863 [(M+H)+], measured value: 669.3860 [(M+H)+].

Provenance & Evidence