Water → HCID 86753598, compound

HRID 343189Notes

Reaction equation

HRID 343189 reaction equation
[O:1]=[C:2]1[N:8]([CH2:9][C:10]([N:12]([CH:19]([CH3:21])[CH3:20])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:11])[C:7]2[CH:22]=[CH:23][CH:24]=[CH:25][C:6]=2[N:5]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:4](=[O:32])[C:3]1([C:44](=[O:46])[NH2:45])[C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([O:41]CC)=[O:40])[CH:34]=1.O.C([O-])([O-])=O.[K+].[K+]>C(O)C>[O:1]=[C:2]1[N:8]([CH2:9][C:10]([N:12]([CH:19]([CH3:20])[CH3:21])[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:11])[C:7]2[CH:22]=[CH:23][CH:24]=[CH:25][C:6]=2[N:5]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:4](=[O:32])[C:3]1([C:44](=[O:46])[NH2:45])[C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([OH:41])=[O:40])[CH:34]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 86753597HCID 86753597, compound

Product 1

HCID 86753598HCID 86753598, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.12 g of 2-[2,4-dioxo-5-phenyl-3-(3-ethoxycarbonylphenyl)-carbamoyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-isopropyl-N-phenyl acetamide, prepared as in Example 1, is dissolved in 5 mL of hot ethanol. 2.5 mL of H2O and 0.13 g of K2CO3 are added and the mixture heated at reflux for 4 h and subsequently concentrated in vacuo. The residue is poured into 20 mL of 1N HCl and extracted with ethyl acetate (×3). The organic extract is washed with brine, dried over MgSO4 and concentrated in vacuo to a white solid. Purification by reverse phase C-18 MPLC (70% methanol/TFA-H2O) gave 99 mg of the title compound as a white powder: mp. 165°-170° C.; 1H NMR (CDCl3, 300 MHz) δ8.6 (s, 1H), 8.05 (s, 1H), 7.92 (d, 1H, J=7), 7.75 (d, 1H, J=7), 7.5-7.2 (m, 14H), 7.15 (t, 1H, J=7), 6.97 (d, 1H, J=7), 5.02 (m, 1H), 4.27 (s, 2H), 4.10 (t, 1H, J=7), 3.20 (d, 2H, J=7), 1.08 (d, 3H, J=7), 1.02 (d, 3H, J=7); low resolution MS (FAB) m/e 605 (MH+); Anal. (C35H32N4O6.0.5 TFA.0.5 H2O) Calc. C, 64.5; H, 5.0; N, 8.4; Found: C, 64.5; H, 5.0; N, 8.3.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 4 h
  3. concentrationsubsequently concentrated in vacuo
  4. additionThe residue is poured into 20 mL of 1N HCl
  5. extractionextracted with ethyl acetate (×3)
  6. extractionThe organic extract
  7. washis washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo to a white solid
  10. customPurification by reverse phase C-18 MPLC (70% methanol/TFA-H2O)

Sources & evidence

ORD record
ord-461bca69531945ccad67395163154607
Source dataset
uspto-grants-1999_01
Patent number
US05859007

Reaction notes

Loading…