HCID 57134771, compound → HCID 11171257, compound

HRID 479026Notes

Reaction equation

HRID 479026 reaction equation
C([O:5][C:6](=[O:16])[CH2:7][C@@H:8]([CH2:14][NH2:15])[C@@H:9]([CH3:13])[CH:10]([CH3:12])[CH3:11])(C)(C)C>Cl>[NH2:15][CH2:14][C@@H:8]([C@@H:9]([CH3:13])[CH:10]([CH3:12])[CH3:11])[CH2:7][C:6]([OH:16])=[O:5]

Participants

3

Reactant 1

HCID 57134771HCID 57134771, compound

Product 1

HCID 11171257HCID 11171257, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of the amine 23 and lactam 24 (500 mg) in 3 M hydrochloric acid were heated to reflux for 9 hours, then stirred at room temperature for 15 hours. The solution was concentrated and the resultant solid subjected to a sequential purification which involved ion exchange chromatography (Dowex 50WX8, strongly acidic), oxalate salt formation then further purification by ion exchange chromatography (Dowex 50WX8, strongly acidic) to give the Example 2 (343 mg) as a white solid. 1H NMR (D2O) δ2.87 (m, 2H), 2.22 (dd, 1H, J=15.4 and 3.4 Hz), 2.12 (m, 1H), 1.93 (dd, 1H, J=15.4 and 9.5 Hz), 1.38 (m, 1H), 1.12 (m, 1H), 0.77 (d, 1H, J=6.6 Hz), 0.74 (d, 1H, J=6.6 Hz), 0.70 (d, 1H, J=6.8 Hz). MS, m/z (relative intensity): 174 [M+H, 100%].

Workup

  1. temperatureto reflux for 9 hours
  2. concentrationThe solution was concentrated
  3. customthe resultant solid subjected to a sequential purification which
  4. customstrongly acidic), oxalate salt formation then further purification by ion exchange chromatography (Dowex 50WX8

Sources & evidence

ORD record
ord-c26fc45850c04746936cd003361d3093
Source dataset
uspto-grants-2003_11
Patent number
US06642398B2

Reaction notes

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