Hydrochloric Acid → HCID 66591058, compound

HRID 2363603Notes

Reaction equation

HRID 2363603 reaction equation
[CH2:1]([N:8]1[CH2:12][C@@H:11]2[C@@H:13]([NH:16][C:17](=[O:32])[C@@H:18]([N:23](C)[C:24](=O)OC(C)(C)C)[CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:14][CH2:15][C@@H:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.O1CCOCC1>>[CH2:1]([N:8]1[CH2:12][C@@H:11]2[C@@H:13]([NH:16][C:17](=[O:32])[C@H:18]([CH2:19][CH:20]([CH3:21])[CH3:22])[NH:23][CH3:24])[CH2:14][CH2:15][C@@H:10]2[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 66589964HCID 66589964, compound

Product 1

HCID 66591058HCID 66591058, compound

Procedure

tert-Butyl(S)-1-((3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-ylamino)-4-methyl-1-oxopentan-2-yl(methyl)carbamate (60 mg, 0.135 mmol) from Example 222 was combined with 4 N hydrogen chloride in 1,4-dioxane (0.698 mL, 2.79 mmol). The reaction was stirred at room temperature for 16 hours and then concentrated. The material was purified using a 12 g silica gel cartridge with a gradient of 1-10% methanol (2 N ammonia)/dichloromethane over 20 minutes to give the title compound: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.16-8.19 (m, 1H), 7.44-7.46 (m, 2H), 7.37 (t, J=7.5 Hz, 2H), 7.28 (t, J=7.3 Hz, 1H), 4.42-4.48 (m, 1H), 3.61 (d, J=13.1 Hz, 1H), 3.46 (d, J=13.1 Hz, 1H), 3.22 (dd, J=8.2, 5.8 Hz, 1H), 2.87 (d, J=10.3 Hz, 1H), 2.51-2.61 (m, 2H), 2.44 (dd, J=8.8, 7.1 Hz, 1H), 2.43 (s, 3H), 2.37 (dd, J=9.0, 2.0 Hz, 1H), 2.25-2.29 (m, 1H), 2.09-2.17 (m, 1H), 1.95-2.07 (m, 1H), 1.82-1.95 (m, 2H), 1.72 (ddd, J=13.5, 7.8, 5.8 Hz, 1H), 1.55-1.64 (m, 2H), 1.38-1.45 (m, 1H), 0.92 (d, J=6.6 Hz, 3H), 0.86 (d, J=6.6 Hz, 3H); MS (ESI+) m/z 344 (M+H)+.

Workup

  1. concentrationconcentrated
  2. customThe material was purified
  3. customover 20 minutes

Sources & evidence

ORD record
ord-e2d6527e8cad42feb9026d974d687555
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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