4-[(tert-Butoxycarbonylamino)methyl]benzoic acid Chemical Properties

Melting point:

164-168 °C

Boiling point:

427.8±38.0 °C(Predicted)

Density 

1.178±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

pka

4.25±0.10(Predicted)

form 

Crystalline

color 

Off-white

BRN 

2854286

CAS DataBase Reference

33233-67-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-36/37/38

Safety Statements 

22-26-36/37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29242990

MSDS

• Language:English Provider:SigmaAldrich

4-[(tert-Butoxycarbonylamino)methyl]benzoic acid Usage And Synthesis

Chemical Properties

white solid

Uses

4-(Boc-aminomethyl)benzoic Acid is the Boc protected form of 4-(Aminomethyl)benzoic Acid (A615230) and is used as a reagent in the synthesis of indoleamide derivatives as EP2 antagonists with high selectivity. 4-(Boc-aminomethyl)benzoic Acid is also used as a reagent in the synthesis of aminopyridine-derived amides as nicotinamide phosphoribosyltransferase inhibitors.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

Phase 1 - Boc Protection: 4-(Aminomethyl)benzoic acid (10.00 g, 65.36 mmol) was stirred with di-tert-butyl dicarbonate (28.0 g, 130.72 mmol) in a solvent mixture of deionized water (100 mL) and tetrahydrofuran (100 mL) at room temperature. The reaction system was adjusted to pH ≈ 6 by slow addition of saturated aqueous sodium bicarbonate solution and the reaction was continuously stirred for 16 hours. Upon completion of the reaction, the reaction solution was carefully acidified to pH ≈ 3 with 1 M hydrochloric acid solution, at which time a white solid precipitated. The solid product was collected by filtration and washed with deionized water and dried to afford 4-[(tert-butoxycarbonylamino)methyl]benzoic acid as a white solid (16.1 g, 97% yield). Mass spectrometry analysis showed m/z = 274 [M + Na]+.

References

[1] Patent: WO2008/53131, 2008, A1. Location in patent: Page/Page column 58; 59-60
[2] Patent: WO2008/40934, 2008, A1. Location in patent: Page/Page column 57-58
[3] Patent: WO2010/20556, 2010, A1. Location in patent: Page/Page column 206
[4] Journal of Medicinal Chemistry, 2016, vol. 59, # 3, p. 965 - 984
[5] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 4, p. 501 - 508

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