1-[(tert-Butoxycarbonyl)amino]cyclopropanecarboxylic acid

White crystalline powder

4.18 g (30.37 mmol) of the 1-aminocyclopropyl acetic acid hydrochloride prepared in Preparational was dissolved in 61 ml of methylene chloride, to which 4.7 ml (33.40 mmol) of TEA was added. The mixture was stirred for 10 minutes and then methylene chloride was evaporated under reduced pressure. The reactant was dissolved in 36.5 ml of 1N NaOH solution and 101 ml of 1, 4-dioxane, to which 8.4 ml (36.44 mmol) of BocBromine (2.0 ml, 40 mmol) was slowly added to a suspension of 1-carbamoylcyclopropanecarboxylic acid (2.56 g, 20 mmol) in 15 ml ofwater in an ice-bathe. After that a solution of NaOH (7.94 g, 199 mmol) in 20 ml of water was added dropwise to the mixture in 1 h and thereaction mixture was stirred at 50°C for 2 h. The mixture was washed with chloroform, cooled to 0°C and acidified to pH 1. Water wasremoved under vacuum and the residue was extracted with isopropanol. The extract was evaporated to give 1-aminocyclopropanecarboxylicacid hydrochloride which was futher used without additional purification. A suspension of 1-aminocyclopropanecarboxylic acidhydrochloride in 40 ml of dioxane was cooled in an ice-bathe and a solution of NaOH (1.83 g, 46 mmol) in 30 ml of water was added to themixture. After stirring for 10 min Boc2O (5.19 g, 24 mmol) was added to the mixture and it was stirred for 3 h at room temperature. Afterthat the mixture was cooled again and treated with 60 ml of choroform, acidified until pH 1 and the organic phase was separated. The waterphase was extracted twice with 30 more ml of chloroform and the combined organic layer was dried over anhydrous MgSO4, filtered andevaporated to give the desired product (1.64 g, 41 percent).#10;To a stirred solution of 1-aminocyclopropane-1-carboxylic acid (4 g, 39.6 mmol) in 1, 4-dioxane: H1-amino cyclopropanecarboxylic acid (0.3 g, 2.96 mmol) was dissolved in a mixture of dioxane (7.0 mL) and NaOH 0.5M (7.0 mL). To a solution of 1-amino-1-cyclopropane-carboxylic acid (ACC) (0.2 g, 1.98 mmol) in dioxane (10 mL)/water (6 mL) was added NaHCO1-Aminocyclopropylcarboxylic acid 5a (5.0 g, 49 mmol) was dissolved in tetrahydrofuran (60 mL)a mixed solvent with 10percent aqueous sodium hydroxide solution (49 mL), Di-tert-butyl dicarbonate (12 mL, 52 mmol) was added dropwise.The reaction was carried out at room temperature for 22 hours.The reaction was quenched by the addition of water (100 mL), and washed with ethyl acetate (100 mL×2). The aqueous phase was adjusted to pH 2 with 4 mol/L hydrochloric acid, and a white solid was precipitated, filtered, and dried.The title compound 5b was obtained as a white solid (7.0 g, yield 70percent).To a stirred solution of 1-aminocyclopropane-l-carboxylic acid (30 g, 149.25 mmol, 1.0 eq) in 1, 4-dioxane (300 ml) at 0 °C was added 2N NaOH solution (300 ml) followed by (Boc)Preparational

Molecular Weight:201.22
XLogP3:0.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:201.10010796
Monoisotopic Mass:201.10010796
Topological Polar Surface Area:75.6
Heavy Atom Count:14
Complexity:263
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes