Potassium Iodide → Tritylolmesartan medoxomil

HRID 554019Notes

Reaction equation

HRID 554019 reaction equation
[OH:1][C:2]([C:5]1[N:6]=[C:7]([CH2:50][CH2:51][CH3:52])[N:8]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]3[N:30]([C:31]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[N:29]=[N:28][N:27]=3)=[CH:16][CH:15]=2)[C:9]=1[C:10]([OH:12])=[O:11])([CH3:4])[CH3:3].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl[CH2:62][C:63]1[O:64][C:65](=[O:69])[O:66][C:67]=1[CH3:68]>CC(C)=O.C1(C)C=CC=CC=1>[CH3:52][CH2:51][CH2:50][C:7]1[N:8]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]3[C:21]([C:26]4[N:30]([C:31]([C:44]5[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=5)([C:38]5[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=5)[C:32]5[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=5)[N:29]=[N:28][N:27]=4)=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:18][CH:19]=2)[C:9]([C:10]([O:12][CH2:68][C:67]2[O:66][C:65](=[O:69])[O:64][C:63]=2[CH3:62])=[O:11])=[C:5]([C:2]([OH:1])([CH3:3])[CH3:4])[N:6]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 98555184-(Chloromethyl)-5-methyl-1,3-dioxol-2-oneHCID 190363054-(2-Hydroxypropan-2-yl)-2-propyl-1-({2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl}methyl)-1H-imidazole-5-carboxylic acid

Product 1

HCID 19036162Tritylolmesartan medoxomil

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 1140TolueneSolvent

Procedure

4-(1-Hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylic acid dehydrate (100 g) was suspended in acetone (1 L) & heated to reflux; the solution obtained was added to suspension of potassium carbonate (15 g), potassium iodide (6 g) & 4-chloromethyl-5-methyl-1,3-dioxol-2-one (35 g) in acetone (500 mL) at reflux temperature. Reaction mass was refluxed for 2-6 hrs. After competition of reaction, the reaction mass was filtered & the acetone was distilled from combined mother liquor. The residue obtained was dissolved in toluene (1 L) toluene layer was washed with brine (3×250 mL). Toluene was removed under reduced pressure & residue thus obtained was recrystallized from methanol to give trityl Olmesartan

Workup

  1. temperatureheated to reflux
  2. customthe solution obtained
  3. temperatureat reflux temperature
  4. customReaction mass
  5. temperaturewas refluxed for 2-6 hrs
  6. customAfter competition of reaction
  7. filtrationthe reaction mass was filtered
  8. distillationthe acetone was distilled
  9. customThe residue obtained
  10. washwas washed with brine (3×250 mL)
  11. customToluene was removed under reduced pressure & residue
  12. customthus obtained
  13. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-27a33cadc84643d582af36ff21d06704
Source dataset
uspto-grants-2011_11
Patent number
US08048904B2

Reaction notes

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