(+)-(1R,4S)-N-BOC-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID

off-white crystalline powder

A mixture of (LR, 4S) -4-amino-cyclopen-2-ene carboxylic acid (130 g, 1.0 mol), water (250 mL), sodium bicarbonate (170 g, 2.0 mol) and THF (750 mL) was stirred for 30 min, then solid di-tert-butyl dicarbonate (230 g, 1.05 mol) was added. The mixture was stirred over the weekend, filtered to remove the insoluble material, evaporated to remove the THF, and cooled to 0 C. To the residue was added 2 N aqueous HC1 (-500 mL) until pH = 3. The resulting precipitate was collected by filtration and washed with water, and dried under vacuum overnight. The desired acid was obtained as a white solid (230 g, 100percent). 1H NMR (400 MHZ, CD30D) : 8 5.95 (m, 1H), 5.79 (m, 1H), 4. 80 (br s, 1H), 3.45 (m, 1H), 2.50 (m, 1H), 1.79 (m, 1H), 1.44 (s, 9H).A mixture of (lR, 4S) -4-amino-cyclopen-2-ene carboxylic acid (127 g, 1.0 mol), water (250 mL), sodium bicarbonate (168 g, 2.0 mol) and THF (750 mL) was stirred for 30 min, then solid Boc20 (230 g, 1.05 mol) was added. The mixture was stirred overweekend, filtered to remove insoluble material, evaporated to remove THF, cooled at 0 °C. To the residue was added 2N aq. HC1 (-500 mL) until pH = 3.0. The resulting precipitate was collected by filtration and washed with water, dried in vacuum overnight. The desired acid was obtained as a white solid (227 g, 100percent). 'H NMR (400 MHz, CD30D) : 5.95 (m, 1H), 5.79 (m, 1H), 4.80 (br s, 1H), 3.45 (m, 1H), 2.50 (m, 1H), 1.79 (m, 1H), 1.44 (s, 9H).Intermediate 4; Procedure A; Step A; A mixture of (1R, 4S)-4-amino-cyclopen-2-ene carboxylic acid (127 g, 1.0 mol), water (250 mL), sodium bicarbonate (168 g, 2.0 mol) and THF (750 mL) was stirred for 30 min, then solid BocProcedure B; Step A; A mixture of (1R, 4S)-4-amino-cyclopen-2-ene carboxylic acid (130 g, 1.0 mol), water (250 mL), sodium bicarbonate (170 g, 2.0 mol) and tetrahydrofuran (750 mL) was stirred for 30 min, then solid di-tert-butyl dicarbonate (230 g, 1.05 mol) was added. The mixture was stirred over the weekend, filtered to remove the insoluble material, evaporated to remove the tetrahydrofuran, and cooled to 0° C. To the residue was added 2 N aqueous HCl until the pH reached 3 (500 mL). The resulting precipitate was collected by filtration and washed with water and dried under vacuum overnight. The desired acid was obtained as a white solid (230 g, 100percent). A mixture of (lR, 4S)-4-mnino-cyclopen-2-ene carboxylic acid (127 g, 1.0 mol), water (250 mL), sodium bicarbonate (168 g, 2.0 mol) and THF (750 mL) was stirred for 30 min, then solid Boc20 (230 g, 1.05 mol) was added. The mixture was stirred overweekend, filtered to remove insoluble material, evaporated to remove THF, cooled at 0 °C. To the residue was added 2N aq. HCI ((at)500 mL) until pH = 3.0. The resulting precipitate was collected by filtration and washed with water, dried in vacuum overnight. The desired acid was obtained as a white solid (227 g, 100percent).

Molecular Weight:227.26
XLogP3:1.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:227.11575802
Monoisotopic Mass:227.11575802
Topological Polar Surface Area:75.6
Heavy Atom Count:16
Complexity:316
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes