Boc-3-Aminomethylbenzoic acid Chemical Properties

Boiling point:

434.6±38.0 °C(Predicted)

Density 

1.178±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

Crystalline Powder or Flakes

pka

4.21±0.10(Predicted)

color 

White to off-white

BRN 

6957774

CAS DataBase Reference

117445-22-4(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29242990

MSDS

• Language:English Provider:SigmaAldrich

Boc-3-Aminomethylbenzoic acid Usage And Synthesis

Chemical Properties

Off-white powder

Uses

3-(Boc-aminomethyl)benzoic Acid is used to synthesize aminodihydroquinazolines as inhibitors of BACE-1 (β-site APP cleaving enzyme). It is also used to prepare spiro[1H-indene-1,4''-piperidine] derivatives as potent and selective non-peptide human somatostatin receptor subtype 2 (sst2) agonists.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

General procedure for the synthesis of 3-(N-Boc-aminomethyl)benzoic acid from methyl 3-(((tert-butoxycarbonyl)amino)methyl)benzoate: to a solution of methyl 3-(((tert-butoxycarbonyl)amino)methyl)benzoate (0.6 g, 2.20 mmol) in tetrahydrofuran (THF, 4 mL) at 25°C was added lithium hydroxide (0.3 g, 9.0 mmol) solution in water (2 mL). The reaction mixture was stirred at 50°C for 4 hours. Upon completion of the reaction, THF was removed by distillation under reduced pressure, the reaction mixture was acidified with acetic acid, and the product was subsequently extracted with ethyl acetate. The organic phase was dried with anhydrous sodium sulfate, filtered and concentrated to give the crude product. The crude product was purified by column chromatography to give 3-(N-Boc-aminomethyl)benzoic acid as a colorless solid (250 mg, 44% yield).

References

[1] Patent: WO2011/21209, 2011, A1. Location in patent: Page/Page column 71; 72
[2] Patent: US2012/101099, 2012, A1. Location in patent: Page/Page column 28-30

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