Acetyl chloride → methyl 2-bromo-D-phenylalaninate hydrochloride
Reaction equation
[C:1]([Cl:4])(=O)C.[Br:5][C:6]1[CH:17]=[CH:16][CH:15]=[CH:14][C:7]=1[CH2:8][C@H:9]([C:11]([OH:13])=[O:12])[NH2:10]>CO>[ClH:4].[Br:5][C:6]1[CH:17]=[CH:16][CH:15]=[CH:14][C:7]=1[CH2:8][C@H:9]([C:11]([O:13][CH3:1])=[O:12])[NH2:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 17.5 °C
Procedure
Add acetyl chloride (562.79 g, 7.17 mol) to methanol (10.00 L) at 0° C. in an appropriate vessel. Heat the mixture to 17.5° C. and stir. After 30 minutes, add 2-bromo-D-phenylalanine (500.00 g, 2.05 moles) and heat to reflux. After 4 hours, cool to 20° C. and remove the solvent under reduced pressure to give the title compound (589 g, 1.96 mol) as an off-white solid. MS (m/z): 258 (M-Cl (79Br)), 260 (M-Cl (81Br)).