Dichloromethane → HCID 19919837, compound

HRID 1648529Notes

Reaction equation

HRID 1648529 reaction equation
FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.O[CH2:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=1.C(N(CC)C(C)C)(C)C.[CH2:37]([N:41]1[C:42](=[O:80])[N:43]([CH2:76][CH2:77][CH2:78][CH3:79])[C:44](=[O:75])/[C:45]/1=[CH:46]/[C:47]1[N:51]=[C:50]([CH2:52][CH2:53][CH2:54][CH3:55])[N:49](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:48]=1)[CH2:38][CH2:39][CH3:40].C(Cl)[Cl:82]>O.C(O)(=O)C>[ClH:82].[CH2:52]([C:50]1[N:51]([CH2:17][C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=2)[C:47](/[CH:46]=[C:45]2\[N:41]([CH2:37][CH2:38][CH2:39][CH3:40])[C:42](=[O:80])[N:43]([CH2:76][CH2:77][CH2:78][CH3:79])[C:44]\2=[O:75])=[CH:48][N:49]=1)[CH2:53][CH2:54][CH3:55]

Participants

8

Reactant 5

HCID 6344Dichloromethane3×HCID 67749Trifluoromethanesulfonic anhydrideHCID 81325Methyl 4-(hydroxymethyl)benzoateHCID 81531DiisopropylethylamineHCID 19919793HCID 19919793, compound

Product 1

HCID 19919837HCID 19919837, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of trifluoromethanesulfonic anhydride (0.094 mL, 0.56 mmol) in methylene chloride (10 mL) at -78° C. was added a solution of methyl 4-(hydroxymethyl)benzoate (0.093g, 0.56 mmol) and N,N-diisopropylethylamine (0.098 mL, 0.56 mmol) in methylene chloride (10 mL) dropwise over 5 minutes. This solution was stirred for 15 minutes and then a solution of Z-1,3-dibutyl-5-[[2-butyl-3-(triphenylmethyl)-3H-imidazol-5-yl]methylene]-2,4imidazolidinedione (0.330g, 0.56 mmol) in methylene chloride (5 mL) was added dropwise. The mixture was allowed to slowly warm to room temperature within the cooling bath overnight. Glacial acetic acid (10 mL) and water (2 mL) were added and the mixture boiled for 1 hour on a steam bath. After evaporation in vacuo the residue was dissolved in ethyl acetate, washed with saturated NaHCO3 and brine, and then dried over MgSO4. Chromatography eluting with CHCl3 afforded the required product with spectral characteristics identical with the product formed in Example 33

Workup

  1. waitthe mixture boiled for 1 hour on a steam bath
  2. customAfter evaporation in vacuo the residue
  3. dissolutionwas dissolved in ethyl acetate
  4. washwashed with saturated NaHCO3 and brine
  5. dry with materialdried over MgSO4
  6. washChromatography eluting with CHCl3

Sources & evidence

ORD record
ord-a266a6f773b444108732db956099e336
Source dataset
uspto-grants-1995_07
Patent number
US05436260

Reaction notes

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