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

HRID 552209Notes

Reaction equation

HRID 552209 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH:15][C:16]([CH:18]3[CH2:22][CH2:21][CH2:20][CH:19]3[NH:23]C(OC(C)(C)C)=O)=[O:17])[CH:14]=1)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH:15][C:16]([C@@H:18]3[CH2:22][CH2:21][CH2:20][C@@H:19]3[NH2:23])=[O:17])[CH:14]=1)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1

Participants

3

Reactant 1

HCID 67165900HCID 67165900, compound

Product 1

HCID 11393321cis-2-amino-cyclopentanecarboxylic acid (6-chloro-9H-beta-carbolin-8-yl)-amideYield 106.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

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). 1H-NMR (300 MHz, DMSO-d6): δ 9.29 (s, 1); 8.75 (d, 1); 8.53 (d, 1); 8.37 (s, 1); 8.02 (s, 1); 4.05-3.95 (m, 1); 3.42-3.34 (m, 1); 2.46-1.80 (m, 6). NH4OAc standard conditions. DAD Rf=1.65 min. M+H=329.

Workup

  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

Sources & evidence

ORD record
ord-3facb587038a4e9f9aa824557eaf4025
Source dataset
uspto-grants-2011_05
Patent number
US07951801B2

Reaction notes

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