Potassium Carbonate → 2-[5-Cyclohexyl-1-(3,3-dimethyl-2-oxo-butyl)-2-oxo-1,2-dihydro-3H-1,3,4-benzotriazepin-3-yl]-N-(3-hydroxymethyl-phenyl)-acetamide

HRID 2113315Notes

Reaction equation

HRID 2113315 reaction equation
COC(=O)[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13](=[O:40])[CH2:14][N:15]2[N:21]=[C:20]([CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]=3[N:17]([CH2:32][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])[C:16]2=[O:39])[CH:7]=1.C([O-])([O-])=O.[K+].[K+]>C1COCC1.CO>[CH:22]1([C:20]2[C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]=3[N:17]([CH2:32][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])[C:16](=[O:39])[N:15]([CH2:14][C:13]([NH:12][C:8]3[CH:9]=[CH:10][CH:11]=[C:6]([CH2:5][OH:4])[CH:7]=3)=[O:40])[N:21]=2)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 11606525Carbonic acid 3-{2-[5-cyclohexyl-1-(3,3-dimethyl-2-oxo-butyl)-2-oxo-1,2-dihydro-3H-1,3,4-benzotriazepin-3-yl]-acetylamino}-benzyl ester methyl ester

Product 1

HCID 116563382-[5-Cyclohexyl-1-(3,3-dimethyl-2-oxo-butyl)-2-oxo-1,2-dihydro-3H-1,3,4-benzotriazepin-3-yl]-N-(3-hydroxymethyl-phenyl)-acetamideYield 89%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Carbonic acid 3-{2-[5-cyclohexyl-1-(3,3-dimethyl-2-oxo-butyl)-2-oxo-1,2-dihydro-3H-1,3,4-benzotriazepin-3-yl]-acetylamino}-benzyl ester methyl ester (Example 48, step a) was dissolved in THF-MeOH (1:1/40 ml) and 1% K2CO3 solution (30 ml) was added. The mixture was stirred at room temperature for 2 h. After concentration of the organic solvents, a precipitate formed, which was collected by filtration and dried in vacuo to afford the title compound as a yellow solid (790 mg, 89%). 1H NMR (CDCl3) 8.31 (1H, s), 7.51-7.45 (3H, m), 7.31-7.28 (3H, m), 7.26-7.10 (2H, m), 4.70 (1H, d), 4.67 (2H, s), 4.64 (1H, d), 4.26 (1H, d), 4.22 (1H, d), 2.89 (1H, m), 1.85-1.55 (6H, m), 1.30-1.24 (13H, m). Found: C, 67.70; H, 7.40; N, 10.79%; C29H36N4O4.0.5H2O requires: C, 67.81; H, 7.26; N, 10.91%.

Workup

  1. customAfter concentration of the organic solvents, a precipitate formed
  2. filtrationwhich was collected by filtration
  3. customdried in vacuo

Sources & evidence

ORD record
ord-dee3fe46cb554a1d85eb20676a466601
Source dataset
uspto-grants-2009_04
Patent number
US07524837B2

Reaction notes

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