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HomeProduct name listN-Boc-1-aminocyclobutanecarboxylic acid

N-Boc-1-aminocyclobutanecarboxylic acid

Synonym(s):1-(Boc-amino)cyclobutanecarboxylic acid;Boc-cyclovaline

N-Boc-1-aminocyclobutanecarboxylic acid Structural

What is N-Boc-1-aminocyclobutanecarboxylic acid?

The Uses of N-Boc-1-aminocyclobutanecarboxylic acid

Boc-1-aminocyclobutane-1-carboxylic Acid is used in the synthesis of dipeptidyl nitriles with cathepsin-inhibiting activities. It is also used to prepare alkyl-oxo-aryl amides as novel antagonists of TRPA1 receptor.

Synthesis

Under stirring, add 1-aminocyclobutylcarboxylic acid (500mg, 4.34mmol) to 10mL of 0.5M sodium hydroxide solution, and add 10mL of 1,4-dioxane and di-tert-butyl dicarbonate (1.42g, 6.51 mmol), react for 15 hours. Extract with diethyl ether (20 mL × 2), add hydrochloric acid dropwise until the pH of the aqueous phase is 4, and extract with ethyl acetate (30 mL × 3). The organic phases were then combined, washed with saturated sodium chloride solution (20mL×2), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to obtain the product N-Boc-1-aminocyclobutanecarboxylic acid (750mg, white solid), yield:80.6%.

Properties of N-Boc-1-aminocyclobutanecarboxylic acid

Melting point: 129-133 °C(lit.)
Boiling point: 362.1±21.0 °C(Predicted)
Density  1.18±0.1 g/cm3(Predicted)
storage temp.  Keep in dark place,Sealed in dry,Room Temperature
solubility  soluble in Methanol
form  Powder
pka 4.14±0.20(Predicted)
color  White to light brown
BRN  7994003
InChI InChI=1S/C10H17NO4/c1-9(2,3)15-8(14)11-10(7(12)13)5-4-6-10/h4-6H2,1-3H3,(H,11,14)(H,12,13)
CAS DataBase Reference 120728-10-1(CAS DataBase Reference)

Safety information for N-Boc-1-aminocyclobutanecarboxylic acid

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405:Store locked up.

Computed Descriptors for N-Boc-1-aminocyclobutanecarboxylic acid

InChIKey ROVVUKFHORPDSM-UHFFFAOYSA-N
SMILES C1(NC(OC(C)(C)C)=O)(C(O)=O)CCC1

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