4-(BOC-AMINO)CYCLOHEXANECARBOXYLIC ACID Chemical Properties

Boiling point:

396.7±31.0 °C(Predicted)

Density 

1.12

storage temp. 

2-8°C

solubility 

Soluble in methanol and tetrahydrofuran(THF).

pka

4.76±0.10(Predicted)

form 

powder to crystal

color 

White to Almost white

Safety Information

WGK Germany 

3

HS Code 

2922498590

MSDS

• Language:English Provider:SigmaAldrich

4-(BOC-AMINO)CYCLOHEXANECARBOXYLIC ACID Usage And Synthesis

Uses

4-(Boc-amino)cyclohexanecarboxylic acid is used as pharmaceutical intermediate.

Synthesis

To a stirred solution of trans-4-aminocyclohexanecarboxylic acid (1 g, 6.98 mmol) in tert-butanol (10 mL) and NaOH (0.307 g, 7.68 mmol) in water (10 mL) was slowly added di-tert-butyl dicarbonate (1.7 g, 7.68 mmol) at 0 °C. The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, hexane (50 mL) was added to the mixture and the pH was adjusted to about 6 with 6 N HCl. Subsequently, the mixture was extracted with ethyl acetate (3 x 50 mL) and the organic phases were combined and washed with saturated brine solution (25 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the white powdery product cis-4-((tert-butoxycarbonyl)amino)cyclohexanecarboxylic acid (1.4 g, 82.8% yield). Mass spectrum (ES-) m/z 242 [M-H]-.

References

[1] Patent: US2017/348315, 2017, A1. Location in patent: Paragraph 0400
[2] Patent: WO2010/45987, 2010, A1. Location in patent: Page/Page column 43-44
[3] European Journal of Medicinal Chemistry, 2001, vol. 36, # 3, p. 265 - 286
[4] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 2, p. 89 - 93

4-(BOC-AMINO)CYCLOHEXANECARBOXYLIC ACID(130309-46-5)Related Product Information

• CIS-2-(BOC-AMINO)-CYCLOHEXANECARBOXYLIC ACID
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