HCID 11772339, compound → (1S,2R,3R,5R,6S)-2-Amino-3-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylic acid

Temperature

23 °C

A solution of (1S,2R,3R,5R,6S)-2-azido-3-hydroxy-bicyclo [3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester (VII-1) (1.55 g, 4.49 mmol) in HOAc (20 mL) and H2O (5 mL) was hydrogenated in the presence of Pd/C (100 mg, 10% Pd/C) at 23° C. for 18 h. The catalyst was removed by filtration, the filter cake washed with 50% aqueous acetic acid. After removal of the solvent in vacuum, the beige residue was refluxed in 10% HCl (55 mL) for 4 h. The solution was cooled to 23° C., filtered, washed with water and evaporated to dryness. The remaining pale yellow solid was dissolved in EtOH (45 mL) and propylene oxide (24 mL) and refluxed for 15 min, whereupon the amino acid precipiated. After cooling to 23° C., the product was filtered off, washed with ether and dried to give (1S,2R,3R,5R,6S)-2-amino-3-hydroxy-bicyclo [3.1.0]hexane-2,6-dicarboxylic acid (I-A) (784 mg, 87%) as a white solid. 1H-NMR (250 MHz, D2O) □1.87 (1H, t, J=3.1 Hz), 2.15-2.26 (3H, m), 2.38 (1H, dd, J=13.0, 7.6 Hz), 3.97 (1H, dd,J=8.6,7.4 Hz); MS[ISP]202 (M+H+); mp>250° C.; □D20 +7.41° (c=1.01, H2O).

1. customThe catalyst was removed by filtration
2. washthe filter cake washed with 50% aqueous acetic acid
3. customAfter removal of the solvent in vacuum
4. temperaturethe beige residue was refluxed in 10% HCl (55 mL) for 4 h
5. filtrationfiltered
6. washwashed with water
7. customevaporated to dryness
8. dissolutionThe remaining pale yellow solid was dissolved in EtOH (45 mL)
9. temperaturepropylene oxide (24 mL) and refluxed for 15 min, whereupon the amino acid
10. temperatureAfter cooling to 23° C.
11. filtrationthe product was filtered off
12. washwashed with ether
13. customdried

ORD record

ord-ec26575883404418b7c2591a8a251c44

Source dataset

uspto-grants-2000_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06107342