Sodium Iodide → HCID 18464433, compound

HRID 2230700Notes

Reaction equation

HRID 2230700 reaction equation
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:26]([N:29]2[CH:33]=[N:32][N:31]=[N:30]2)=[CH:25][C:4]=1[C:5]([N:7]1[CH2:11][CH2:10][C:9]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([CH2:12][CH2:13]OS(C)(=O)=O)[CH2:8]1)=[O:6].I.[OH:35][CH2:36][CH2:37][N:38]1[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=2[N:40]=[C:39]1[N:47]1[CH2:53][CH2:52][CH2:51][NH:50][CH2:49][CH2:48]1.[I-].[Na+].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C(#N)C.CO.ClCCl.ClCCl>[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:26]([N:29]2[CH:33]=[N:32][N:31]=[N:30]2)=[CH:25][C:4]=1[C:5]([N:7]1[CH2:11][CH2:10][C:9]([CH2:12][CH2:13][N:50]2[CH2:51][CH2:52][CH2:53][N:47]([C:39]3[N:38]([CH2:37][CH2:36][OH:35])[C:42]4[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=4[N:40]=3)[CH2:48][CH2:49]2)([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:8]1)=[O:6]

Participants

9

Reactant 5

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 184648112-methoxy-5-(1H-tetrazol-1-yl)benzoyl-3-phenyl-3-(2-methanesulfonyloxyethyl)-pyrrolidineHCID 86583903HCID 86583903, compound

Product 1

HCID 18464433HCID 18464433, compound

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolvent3×

Procedure

Combine 1-(2-methoxy-5-(1H-tetrazol-1-yl)benzoyl)-3-phenyl-3-(2-methanesulfonyloxyethyl)pyrrolidine (prepared from (−)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine (R,R)-di-p-anisoyltartaric acid salt)(0.40 g, 0.85 mmol), 4-(1-(2-hydroxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepane hydriodic acid salt (0.44 g, 0.85 mmol) (1.51 g, 3.2 mmol), sodium iodide (0.127 g, 0.84 mmol), and triethylamine (0.59 mL, 4.23 mmol) in acetonitrile (20 mL). Heat to reflux. After 30 hours, cool to ambient temperature and evaporate in vacuo, and partition the evaporated reaction mixture between dichloromethane and a saturated aqueous sodium bicarbonate solution. Separate the organic layer and extract three times with water. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with dichloromethane, 5% methanol/dichloromethane, 10% methanol/dichloromethane, and then 25% methanol/dichloromethane to give the title compound.

Workup

  1. temperatureHeat to reflux
  2. customevaporate in vacuo
  3. custompartition
  4. customthe evaporated reaction mixture between dichloromethane
  5. customSeparate the organic layer
  6. extractionextract three times with water
  7. dry with materialDry the organic layer over MgSO4
  8. filtrationfilter
  9. customevaporate in vacuo
  10. customto give a residue

Sources & evidence

ORD record
ord-9aa6f1027d9a485aaa0aae283e6cfc1b
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

Loading…