1-tert-Butoxycarbonylaminocyclopentanecarboxylic acid

white to off-white crystalline powder

To a 250 mL round bottom flask was added cycloleucine (1. 0g, 7. [74MMOL), ] [ET3N] (5.4mL, 38. [7MMOL)] 1M NaOH (7.74mL, 7. [74MMOL)] and [CH3CN] (10mL). The clear solution was cooled down to [0°C] and to it was added [(BOC)] [2O.] The reaction was warmed to room temperature and stirred for four hours, during which time a white precipitate formed. The reaction mixture was concentrated and the residue was dissolved in EtOAc: water (1: 1) [(100ML).] The organic phase was washed with water and the aqueous phases were combined and treated with 10percent HCI and then were extracted with EtOAc three times. The combined organic phase was washed successively with water, brine, dried over [MGS04, ] filtered and concentrated to yield the title compound as a white solid (1.29g, 73percent).To a stirred solution of 1-aminocyclopentane-1-carboxylic acid (6 g, 46 mmol) in 1, 4- dioxane: HTo a stirred solution of 1-aminocyclopentane-l-carboxylic acid (10 g, 77.51 mmol, 1.0 eq) in 1, 4-dioxane (100 ml) at 0 °C was added 2N NaOH solution (100 ml) followed by (Boc)1-tert-Butoxycarbonylamino-cyclopentanecarboxylic acid Synthesis of Compound 20; 20.(R).; To 1-amino-l-cyclopentane carboxylic acid (100 mg, 0.774 mmol) in dry acetonitrile (10 ml) was added tetramethylammonium hydroxide pentahydrate (190 mg, 1.04 mmol) and the mixture stirred at room temperature until the acid had dissolved. Boc anhydride (300 mg, 1.37 mmol) was then added and the resultant solution stirred for four days. The solvent was then removed and the resultant residue partitioned between water and ether. The aqueous layer was washed with an additional portion of ether and then acidified with solid citric acid to pH 3-4. The aqueous layer was then back-extracted with ethyl acetate (3 x 15 ml), before being combined, dried (MgSOa

Molecular Weight:229.27
XLogP3:1.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:229.13140809
Monoisotopic Mass:229.13140809
Topological Polar Surface Area:75.6
Heavy Atom Count:16
Complexity:287
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes