Acetic Acid → HCID 58857966, compound

HRID 1162326Notes

Reaction equation

HRID 1162326 reaction equation
[Si]([O:8][CH2:9][C:10]1[N:14]2[C:15](=[O:42])[N:16]([CH:18]3[CH2:23][CH2:22][N:21]([C:24]([C@H:26]([NH:31][C:32]([NH:34][C:35]4[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=4)=[O:33])[C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]3)[CH2:17][C:13]2=[CH:12][N:11]=1)(C(C)(C)C)(C)C.C(O)(=O)C.O>C1COCC1>[Cl:41][C:38]1[CH:37]=[CH:36][C:35]([NH:34][C:32]([NH:31][C@@H:26]([C:24]([N:21]2[CH2:22][CH2:23][CH:18]([N:16]3[CH2:17][C:13]4=[CH:12][N:11]=[C:10]([CH2:9][OH:8])[N:14]4[C:15]3=[O:42])[CH2:19][CH2:20]2)=[O:25])[C:27]([CH3:29])([CH3:30])[CH3:28])=[O:33])=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 68647159HCID 68647159, compound

Product 1

HCID 58857966HCID 58857966, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-((1R)-1-((4-(5-(((tert-butyldimethylsilyl)oxy)methyl)-3-oxo-1H-imidazo[1,5-c]imidazol-2(3H)-yl)-1-piperidinyl)carbonyl)-2,2-dimethylpropyl)-N′-(4-chlorophenyl)urea (0.31 g) obtained in Example 831) was dissolved in a solution (acetic acid:water:THF=4:1:1, 6 ml), and mixed at 60° C. for 4 hours. The solvent was distilled off under reduced pressure, and then to the residue were added ethyl acetate and a saturated aqueous sodium hydrogen carbonate solution. The organic layer was collected by separation, washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with basic silica gel column (ethyl acetate to ethyl acetate:ethanol=10:1) to obtain the title compound as a colorless solid (0.21 g, 85%).

Workup

  1. additionmixed at 60° C. for 4 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. additionto the residue were added ethyl acetate
  4. customThe organic layer was collected by separation
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified with basic silica gel column (ethyl acetate to ethyl acetate:ethanol=10:1)

Sources & evidence

ORD record
ord-9fef2a1df8c54e1592186a2fa8efc169
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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