Hydrochloric Acid → HCID 25258315, compound
Reaction equation
[SH:1][CH2:2][CH:3]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Br:14])[CH:9]=1)[C:4]([OH:6])=[O:5].Cl>CC(O)(C)C>[C:3]([S:1][CH2:2][CH:3]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Br:14])[CH:9]=1)[C:4]([OH:6])=[O:5])([CH3:7])([CH3:4])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To the reaction mixture of step 5, under N2 atmosphere, was injected a mixture of t-BuOH (3 ml) and 37% HCl (2.5 ml). The reaction mixture was heated to reflux for 4 hours, then cooled to room temperature and partitioned between water and CH2Cl2. The combined CH2Cl2 phases were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography eluting with 0 to 5% EtOH in CH2Cl2 to give 2-(S-t-butylsulfanylmethyl)-3-(3-bromophenyl)propionic acid as a colorless, viscous oil, 0.133 g, 51%: HPLC purity: 94.5%, MS (ES−) [M−H+]: 329, 331.