HCID 57642292, compound → HCID 16733463, compound

HRID 2113318Notes

Reaction equation

HRID 2113318 reaction equation
C(OC([N:8]([CH2:44][C:45]([OH:47])=[O:46])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][C:16](=[O:43])[CH2:17][N:18]2[N:24]=[C:23]([CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[C:22]3[CH:31]=[CH:32][CH:33]=[CH:34][C:21]=3[N:20]([CH2:35][C:36](=[O:41])[C:37]([CH3:40])([CH3:39])[CH3:38])[C:19]2=[O:42])[CH:10]=1)=O)(C)(C)C>FC(F)(F)C(O)=O>[CH:25]1([C:23]2[C:22]3[CH:31]=[CH:32][CH:33]=[CH:34][C:21]=3[N:20]([CH2:35][C:36](=[O:41])[C:37]([CH3:40])([CH3:39])[CH3:38])[C:19](=[O:42])[N:18]([CH2:17][C:16]([NH:15][C:11]3[CH:10]=[C:9]([NH:8][CH2:44][C:45]([OH:47])=[O:46])[CH:14]=[CH:13][CH:12]=3)=[O:43])[N:24]=2)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1

Participants

3

Reactant 1

HCID 57642292HCID 57642292, compound

Product 1

HCID 16733463HCID 16733463, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

[tert-Butoxycarbonyl-(3-{2-[5-cyclohexyl-1-(3,3-dimethyl-2-oxo-butyl)-2-oxo-1,2-dihydro-3H-1,3,4-benzotriazepin-3-yl]-acetylamino}-phenyl)-amino]-acetic acid (Example 51)(137 mg, 0.21 mmol) was stirred in trifluoroacetic acid for 2 h at room temperature. After concentration, the resulting gum was dissolved in DCM, washed with saturated NaHCO3 and then with 1N HCl. The organic phase was dried over MgSO4, filtered and the solvent was evaporated to afford the title compound as a yellow solid (85 mg, 73%). 1H NMR (DMSO-d6) 9.47 (1H, s), 7.55-7.27 (2H, m), 7.23-7.15 (2H, m), 6.97 (1H, t), 6.92-6.68 (2H, m), 6.25 (1H, m), 5.80 (2H, br s), 4.78 (2H, m), 4.25 (1H, d), 3.95 (1H, d), 3.72 (2H, s), 2.80 (1H, m), 1.86-1.51 (6H, m), 1.26-1.09 (13H, m). The compound was further characterised as the N-methyl-D-glucamine salt. Found: C, 57.66; H, 7.45; N, 9.07%; C30H36N4O6.C7H17NO5.1.5H2O requires: C, 57.65; H, 7.32; N, 9.09%.

Workup

  1. concentrationAfter concentration
  2. dissolutionthe resulting gum was dissolved in DCM
  3. washwashed with saturated NaHCO3
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-719abfed0da74f23a603220f46766a1c
Source dataset
uspto-grants-2009_04
Patent number
US07524837B2

Reaction notes

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