1,4-Dioxane → HCID 66996529, compound

HRID 2363634Notes

Reaction equation

HRID 2363634 reaction equation
[CH3:1][N:2]([C@@H:10]([CH2:32][CH:33]([CH3:35])[CH3:34])[C:11](=[O:31])[NH:12][C@@H:13]1[C@@H:20]2[C@@H:16]([CH2:17][N:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]([F:30])([F:29])[F:28])[CH2:19]2)[CH2:15][CH2:14]1)C(=O)OC(C)(C)C.O1CCOCC1>Cl>[CH3:1][NH:2][C@H:10]([C:11]([NH:12][C@@H:13]1[C@@H:20]2[C@@H:16]([CH2:17][N:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]([F:28])([F:30])[F:29])[CH2:19]2)[CH2:15][CH2:14]1)=[O:31])[CH2:32][CH:33]([CH3:35])[CH3:34]

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 66996989HCID 66996989, compound

Product 1

HCID 66996529HCID 66996529, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

In a 4 mL vial tert-butyl methyl((S)-4-methyl-1-oxo-1-((3aR,4S,6aS)-2-(2-(trifluoromethyl)phenyl)octahydrocyclopenta[c]pyrrol-4-ylamino)pentan-2-yl)carbamate from Step 3 (40 mg, 0.080 mmol) was dissolved in 4 N HCl in 1,4-dioxane (1 mL, 4.00 mmol). An oil slowly gummed out of the solution. The reaction was stirred at ambient temperature for 18 hours, and then the solvent was removed under a stream of nitrogen. The crude material was purified using a 4 g silica gel cartridge with 1-10% methanol (2 N ammonia)/dichloromethane to give N2-methyl-N-{(3aR,4S,6aS)-2-[2-(trifluoromethyl)phenyl]octahydrocyclopenta[c]pyrrol-4-yl}-L-leucinamide: 1H NMR (400 MHz, pyridine-d5) δ ppm 8.28 (d, J=5.2, 1H), 7.66 (d, J=7.8, 1H), 7.46 (t, J=7.4, 1H), 7.27 (d, J=8.3, 1H), 7.11 (t, J=7.7, 1H), 4.56-4.46 (m, 1H), 3.47 (d, J=9.3, 1H), 3.30-3.23 (m, 1H), 3.16-3.09 (m, 1H), 3.02-2.91 (m, 2H), 2.68 (dd, J=14.4, 10.2, 2H), 2.45 (s, 3H), 2.20 (dd, J=11.1, 5.9, 1H), 2.00-1.86 (m, 2H), 1.79-1.70 (m, 1H), 1.69-1.54 (m, 3H), 0.93 (d, J=6.5, 3H), 0.86 (d, J=6.5, 3H); MS (ESI+) m/z 398 (M+H)+.

Workup

  1. customthe solvent was removed under a stream of nitrogen
  2. customThe crude material was purified

Sources & evidence

ORD record
ord-6cf0cf15a81243eb901a5f840d79cf82
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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