Hydrogen Bromide → Carboxymethyl 5-amino-4-oxopentanoate hydrobromide
Reaction equation
[BrH:1].C([NH:9][CH2:10][C:11](=[O:25])[CH2:12][CH2:13][C:14]([O:16][CH2:17][C:18]([O:20]C(C)(C)C)=[O:19])=[O:15])(OC(C)(C)C)=O>C(O)(=O)C>[BrH:1].[NH2:9][CH2:10][C:11](=[O:25])[CH2:12][CH2:13][C:14]([O:16][CH2:17][C:18]([OH:20])=[O:19])=[O:15]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A 30% solution of hydrogen bromide in acetic acid (12 mL) was added to the product of 1a (3.3 g; 9.5 mmol) cooled with an ice-water bath and stirred until the oil dissolved with evolution of gas. After stirring for 15 min, the mixture was triturated with hexane (4×20 mL) and diethyl ether (4×20 mL); the oil solidified to a tan powder. The residue was filtered and dried overnight in a drying pistol at ˜50° C. and 12 mm Hg. 4.44 g (92%) product was obtained (tan powder, mp 110-114° C. (dec.)).