Methanol → 3-Aminomethyl-5-chloro-4-fluoro-benzoic acid methyl ester

HRID 1527472Notes

Reaction equation

HRID 1527472 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([F:11])=[C:6]([CH2:12][NH:13]C(OC(C)(C)C)=O)[CH:5]=1.C(O)(C(F)(F)F)=O.CO>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([F:11])=[C:6]([CH2:12][NH2:13])[CH:5]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 682835653-(tert-Butoxycarbonylamino-methyl)-5-chloro-4-fluoro-benzoic acid methyl ester

Product 1

HCID 682839273-Aminomethyl-5-chloro-4-fluoro-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(tert-butoxycarbonylamino-methyl)-5-chloro-4-fluoro-benzoic acid methyl ester (4.25 g, 13.4 mmol) in CH2Cl2 (70 mL) was added TFA (10.3 mL, 134 mmol), and stirring was continued at RT overnight. Methanol was then added to the reaction mixture, and volatiles were removed in vacuo. The residue was taken up in methanol and concentrated again under reduced pressure to afford the title compound as a beige solid. MS (LC/MS): 218.0 [M+H]+; tR (HPLC conditions c): 3.10 min. The material thus obtained was used in the next reaction step without further purification.

Workup

  1. customwere removed in vacuo
  2. concentrationconcentrated again under reduced pressure

Sources & evidence

ORD record
ord-c6f8844dda9e48489b2bb2b724897a53
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

Loading…