HCID 67165900, compound → cis-2-amino-cyclopentanecarboxylic acid (6-chloro-9H-beta-carbolin-8-yl)-amide

A solution of 2-(tert-butoxycarbonylamino)-cyclopentanecarboxylic acid (6-chloro-9H-β-carbolin-8-yl) amide (736 mg, 1.72 mmol) in trifluoroacetic acid (5 ml) was stirred at RT for 20 min, then concentrated to an orange oil. The oil was dissolved in MeOH (5 ml) and neutralized with a saturated aqueous sodium bicarbonate solution (25 ml). The resulting mixture was further diluted with H2O (25 ml) and EtOAc (100 ml). The aqueous layer was removed and extracted with EtOAc (100 ml). The organic layers were combined, washed with brine, dried over MgSO4, filtered and concentrated to yellow solids (507 mg). These solids were dissolved in MeOH (5 ml) and a solution of HCl in dioxane (4 M, 1.5 ml) was added. The bright yellow solution was stirred 30 min, then concentrated to yield cis-2-amino-cyclopentanecarboxylic acid (6-chloro-9H-β-carbolin-8-yl)-amide as a yellow powder (600 mg).

1. concentrationconcentrated to an orange oil
2. dissolutionThe oil was dissolved in MeOH (5 ml)
3. additionThe resulting mixture was further diluted with H2O (25 ml) and EtOAc (100 ml)
4. customThe aqueous layer was removed
5. extractionextracted with EtOAc (100 ml)
6. washwashed with brine
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated to yellow solids (507 mg)
10. dissolutionThese solids were dissolved in MeOH (5 ml)
11. additiona solution of HCl in dioxane (4 M, 1.5 ml) was added
12. concentrationconcentrated

ORD record

ord-d432fcaf3af3447bbf3a4599b44cc9a3

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07727985B2