Hydrochloric Acid → N1-{(3aS,4R,6aR)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}-L-leucinamide

HRID 2363516Notes

Reaction equation

HRID 2363516 reaction equation
C(OC([NH:8][C@H:9]([C:14]([NH:16][C@H:17]1[C@H:24]2[C@H:20]([CH2:21][N:22]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=3)[CH2:23]2)[CH2:19][CH2:18]1)=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])=O)(C)(C)C.Cl>C(O)C>[F:34][C:32]([F:33])([F:35])[C:28]1[CH:27]=[C:26]([CH:31]=[CH:30][CH:29]=1)[CH2:25][N:22]1[CH2:23][C@H:24]2[C@H:17]([NH:16][C:14](=[O:15])[C@H:9]([CH2:10][CH:11]([CH3:12])[CH3:13])[NH2:8])[CH2:18][CH2:19][C@H:20]2[CH2:21]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66590495N2-(tert-butyloxycarbonyl)-N1-{(3aS,4R,6aR)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}-L-leucinamide

Product 1

HCID 66590662N1-{(3aS,4R,6aR)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}-L-leucinamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N2-(tert-Butyloxycarbonyl)-N1-{(3aS,4R,6aR)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}-L-leucinamide from Step A (0.731 g, 1.469 mmol) in ethanol (5 mL) was treated with HCl (4 N in dioxane, 10.0 mL, 40.0 mmol). The reaction was stirred at room temperature for 2 hours and the solvent removed in vacuo. The reaction was quenched with saturated aqueous sodium bicarbonate and extracted with 3×50 mL of dichloromethane. The solvent was removed in vacuo to give N1-{(3aS,4R,6aR)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}-L-leucinamide: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.27 (d, J=7.6, 1H), 7.75 (s, 1H), 7.63-7.54 (m, 2H), 7.44 (dd, J=6.9, 14.6, 1H), 4.44-4.33 (m, 1H), 3.62-3.53 (m, 2H), 3.45 (d, J=13.5, 1H), 2.84 (dd, J=2.5, 8.9, 1H), 2.52 (dd, J=7.2, 14.0, 1H), 2.50-2.43 (m, 1H), 2.42-2.37 (m, 1H), 2.32 (dd, J=2.8, 9.0, 1H), 2.23 (dd, J=7.2, 8.8, 1H), 2.09 (td, J=6.0, 12.0, 2H), 1.94-1.81 (m, 4H), 1.61-1.50 (m, 2H), 1.39 (ddt, J=6.3, 8.7, 12.6, 1H), 0.90 (d, J=6.4, 3H), 0.84 (d, J=6.3, 3H); MS (ESI+) m/z 398 (M+H)+.

Workup

  1. customthe solvent removed in vacuo
  2. customThe reaction was quenched with saturated aqueous sodium bicarbonate
  3. extractionextracted with 3×50 mL of dichloromethane
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-8981cb14040440a7914c1469d2acab7a
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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