Trans-4-(Boc-amino)cyclohexanecarboxylic acid Chemical Properties

Melting point:

181.0 to 185.0 °C

Boiling point:

396.7±31.0 °C(Predicted)

Density 

1.12±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform, Methanol (Slightly)

pka

4.76±0.10(Predicted)

form 

Powder

color 

White

BRN 

7641071

InChI

InChI=1S/C12H21NO4/c1-12(2,3)17-11(16)13-9-6-4-8(5-7-9)10(14)15/h8-9H,4-7H2,1-3H3,(H,13,16)(H,14,15)/t8-,9-

InChIKey

KXMRDHPZQHAXML-KYZUINATSA-N

SMILES

[C@@H]1(C(O)=O)CC[C@@H](NC(OC(C)(C)C)=O)CC1

CAS DataBase Reference

53292-89-0(CAS DataBase Reference)

Safety Information

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29242990

MSDS

• Language:English Provider:SigmaAldrich

Trans-4-(Boc-amino)cyclohexanecarboxylic acid Usage And Synthesis

Chemical Properties

White solid

Uses

Trans-4-(Boc-amino)cyclohexanecarboxylic acid is a reagent to synthesize N-myristoyltransferase and CD38 inhibitors.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Chemical Reactivity

Trans-4-(Boc-amino)cyclohexanecarboxylic acid is stable under normal conditions, it reacts with strong oxidizing agents.

Synthesis

1. To a stirred aqueous solution (10 mL) of trans-4-aminocyclohexanecarboxylic acid (1 g, 6.98 mmol) in tert-butanol (10 mL) and NaOH (0.307 g, 7.68 mmol) at 0 °C was slowly added di-tert-butyl dicarbonate (1.7 g, 7.68 mmol). 2. The reaction mixture was gradually warmed to room temperature with continuous stirring overnight. 3. Upon completion of the reaction, hexane (50 mL) was added to the mixture and the pH was adjusted to about 6 with 6N HCl. 4. 4. The reaction mixture was extracted with ethyl acetate (3 x 50 mL), the organic phases were combined and washed with brine solution (25 mL). 5. The organic phase was concentrated under pressure to give the white solid product cis-4-((tert-butoxycarbonyl)amino)cyclohexanecarboxylic acid (1.4 g, 82.8% yield). 6. The product was confirmed by mass spectrometry (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

Trans-4-(Boc-amino)cyclohexanecarboxylic acid(53292-89-0)Related Product Information

• trans-4-Dimethylaminocrotonic acid hydrochloride
• Trans-4-(Maleimidomethyl)cyclohexanecarboxylic Acid
• trans-4-Aminocyclohexanemethanol
• 1-Cyclohexene-1-carboxylicacid,4-(aminomethyl)-(9CI)
• TERT-BUTYL TRANS-4-AMINOCYCLOHEXYLMETHYLCARBAMATE
• 1-METHYL-PROP-2-YNYLAMINE HYDROCHLORIDE
• Methyl trans-4-(tert-butoxycarbonylamino)cyclohexanecarboxylate
• BOC-TRANS-4-AMINOCYCLOHEXANOL
• Cyclohexylamine
• 4-AMINOCYCLOHEXANECARBOXYLIC ACID
• BOC-1,4-TRANS-ACHC-OH
• BOC-1,2-TRANS-ACHC-OH
• 7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]heptane-1-carboxylic acid
• 4-TERT-BUTOXYCARBONYLAMINO-CUBANE-1-CARBOXYLIC ACID
• 4-(TERT-BUTOXYCARBONYLAMINO)BICYCLO[2.2.2]OCTANE-1-CARBOXYLIC ACID
• 4-(BOC-AMINO)CYCLOHEXANECARBOXYLIC ACID
• METHYL 4-(TERT-BUTYLCARBONYLAMINO)CUBANECARBOXYLATE
• FMOC-1, 1-ACCH(4-AMINO-BOC)