Diisopropylethylamine → HCID 18464460, compound

HRID 637086Notes

Reaction equation

HRID 637086 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:26]=[C:27]([O:31][CH3:32])[C:28]=1[O:29][CH3:30])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([CH2:13][CH2:14]OS(C)(=O)=O)[CH2:9]1)=[O:7].I.[O:34]=[C:35]([CH3:55])[CH2:36][CH2:37][CH2:38][N:39]1[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=2[N:41]=[C:40]1[N:48]1[CH2:54][CH2:53][CH2:52][NH:51][CH2:50][CH2:49]1.C(N(CC)C(C)C)(C)C.CO.ClCCl>C(#N)C>[CH3:32][O:31][C:27]1[CH:26]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:28]=1[O:29][CH3:30])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH2:13][CH2:14][N:51]2[CH2:52][CH2:53][CH2:54][N:48]([C:40]3[N:39]([CH2:38][CH2:37][CH2:36][C:35](=[O:34])[CH3:55])[C:43]4[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=4[N:41]=3)[CH2:49][CH2:50]2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:9]1)=[O:7]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 184646303,4,5-Trimethoxybenzoyl-3-phenyl-3-(2-methanesulfonyloxyethyl)pyrrolidineHCID 21226129Dichloromethane methanolHCID 86583893HCID 86583893, compound

Product 1

HCID 18464460HCID 18464460, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Combine 1-(3,4,5-trimethoxybenzoyl)-3-phenyl-3-(2-methanesulfonyloxyethyl)pyrrolidine (prepared from (−)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine(R,R)-di-p-anisoyltartaric acid salt) (0.40 g, 0.72 mmol), 4-(1-(4-oxopentyl)-1H-benzimidazol-2-yl)[1,4]diazepane hydriodic acid salt (0.30 g, 0.65 mmol), and N,N-diisopropylethylamine (0.52 mL, 3.02 mmol) in acetonitrile (10 mL). Heat to reflux. After 24 hours, cool and partition the reaction mixture between ethyl acetate and a half saturated aqueous sodium bicarbonate solution. Separate the organic layer extract with a saturated aqueous sodium bicarbonate solution and then brine. Dry the organic layer over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluting with 10% methanol/dichloromethane/0.1% concentrated aqueous ammonia solution to give the title compound: Rf=0.45 (silica gel, 10% methanol/dichloromethane/0.1% concentrated aqueous ammonia solution).

Workup

  1. temperatureHeat to reflux
  2. temperaturecool
  3. custompartition the reaction mixture between ethyl acetate
  4. customSeparate the organic layer
  5. extractionextract with a saturated aqueous sodium bicarbonate solution
  6. dry with materialDry the organic layer over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate in vacuo
  9. customto obtain a residue

Sources & evidence

ORD record
ord-ac0d2c80ae754e50b3922b21a6508a69
Source dataset
uspto-grants-2001_02
Patent number
US06194406B1

Reaction notes

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