Hydrochloric Acid → HCID 66590779, compound

HRID 2363513Notes

Reaction equation

HRID 2363513 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>CCOCC>[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 67449066HCID 67449066, compound

Product 1

HCID 66590779HCID 66590779, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

N2-(tert-butyloxycarbonyl)-N1-{(3aR*,4R*,6aS*)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}-L-leucinamide (140 mg, 0.281 mmol) from Example 137 and 2 N HCl (2.5 mL, 5.00 mmol) were combined in ether (0.5 mL), and the reaction was stirred at room temperature overnight. The solids were collected and dried to give the title compound as the hydrochloride salt: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.59 (s, 0.5H), 8.48 (s, 0.5H), 7.89 (s, 0.5H), 7.83 (s, 0.5H), 7.69 (t, J=6.8, 1H), 7.60 (d, J=7.8, 1H), 7.50-7.44 (m, 1H), 4.96 (br s, 2H), 4.57-4.48 (m, 1H), 3.73 (d, J=13.2, 0.5H), 3.67 (s, 1H), 3.64 (d, J=13.2, 1H), 3.39 (d, J=13.1, 0.5H), 3.35 (d, J=13.2, 0.5H), 2.81-2.70 (m, 2H), 2.45 (dd, J=7.5, 15.3, 1H), 2.39-2.31 (m, 1H), 2.27-2.14 (m, 2H), 1.95-1.79 (m, 2.5H), 1.72-1.56 (m, 2H), 1.53-1.46 (m, 0.5H), 1.33-1.23 (m, 1.5H), 0.90 (dt, J=6.2, 14.1, 6H); MS (ESI+) m/z 398 (M+H)+.

Workup

  1. customThe solids were collected
  2. customdried

Sources & evidence

ORD record
ord-569b8319d15145a98c29e642f66caaea
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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