Reaction #535296

Reaction equation

HCl H2O

CBz-Cl

2-Amino-5-chlorobenzoic acid methyl ester

→

2-benzyloxycarbonylamino-5-chloro-benzoic acid methyl ester

Yield 70.0%

Solvents

pyridine

Conditions

Workup

1. 1
   workup.ADDITIONThe reaction mixture was subsequently poured in a slow stream into 200 mL
2. 2
   OtherThe mixture was transferred to a separatory funnel
3. 3
   Extractionextracted with 2×50 mL of EtOAc
4. 4
   Dryingthe combined organics were dried over sodium sulfate
5. 5
   Concentrationconcentrated in vacuo

Procedure

2-Amino-5-chlorobenzoic acid methyl ester (5 g, 27 mmol) was dissolved in 36 mL pyridine. CBz-Cl (4.2 mL, 29.6 mmol) was then added and the resultant solution was stirred at 60° C. overnight. The following day, LCMS analysis indicated the reaction was complete. The reaction mixture was subsequently poured in a slow stream into 200 mL of rapidly stirring 2 M HCl/H2O. The mixture was transferred to a separatory funnel and extracted with 2×50 mL of EtOAc. The aqueous phase was discarded and the combined organics were dried over sodium sulfate and concentrated in vacuo to provide 6 g of 2-benzyloxycarbonylamino-5-chloro-benzoic acid methyl ester (pale yellow oil, 70% yield): HPLC retention time=3.15 minutes; MS (ES) M+H expected 320.0, found 320.0.

Source