Dimethyl Sulfoxide → HCID 59831615, compound

HRID 268806Notes

Reaction equation

HRID 268806 reaction equation
[H-].[Na+].[CH3:3][S:4]([CH3:6])=[O:5].[C:7]([O:11][C:12](=[O:33])[N:13]([CH2:15][CH2:16][CH:17]([C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[NH:29][CH:28]=[CH:27]2)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:14])([CH3:10])([CH3:9])[CH3:8].[CH3:34][S:35](Cl)(=[O:37])=[O:36].CC[O:41]CC>>[C:7]([O:11][C:12](=[O:33])[N:13]([CH2:15][CH2:16][CH:17]([C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[N:29]([S:35]([CH3:34])(=[O:37])=[O:36])[CH:28]=[CH:27]2)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:14])([CH3:10])([CH3:8])[CH3:9].[C:7]([O:11][C:12](=[O:33])[N:13]([CH2:15][CH2:16][CH:17]([C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[N:29]([S:35]([CH3:34])(=[O:37])=[O:36])[CH:28]=[C:3]2[S:4]([CH3:6])(=[O:41])=[O:5])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:14])([CH3:10])([CH3:9])[CH3:8]

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 59831872HCID 59831872, compound

Product 2

HCID 59831615HCID 59831615, compoundHCID 59831813HCID 59831813, compound

Procedure

A suspension of NaH (23.4 mg, 0.928 mmol) in DMSO (1.2 ml, 16.9 mmol) was stirred at RT for 20 min. To this mixture was added a solution of [3-(1H-indol-5-yl)-3-phenyl-propyl]-methyl-carbamic acid tert-butyl ester LXXV (307 mg, 0.843 mmol) in Et2O (9 ml). The reaction mixture was stirred at room temperature for 40 minutes, after which MsCl (78.2 μl, 1.01 mmol) was added. The reaction mixture was stirred at room temperature for 2.5 hours followed by reflux for 2 hours. The mixture was partitioned between a saturated solution of NaHCO3 and Et2O. The aqueous layer was extracted with Et2O, and the combined organic layers were dried over Na2SO4, filtered, concentrated, and purified via flash chromatography (hexane/EtOAc) affording [3-(1-Methanesulfonyl-1H-indol-5-yl)-3-phenyl-propyl]-methyl-carbamic acid tert-butyl ester LXXVI (56 mg, 15% yield) in a first fraction, and [3-(1,3-Bis-methanesulfonyl-1H-indol-5-yl)-3-phenyl-propyl]-methyl-carbamic acid tert-butyl ester LXXVII (45 mg, 10% yield) in a second fraction.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 40 minutes
  2. stirringThe reaction mixture was stirred at room temperature for 2.5 hours
  3. temperatureby reflux for 2 hours
  4. customThe mixture was partitioned between a saturated solution of NaHCO3 and Et2O
  5. extractionThe aqueous layer was extracted with Et2O
  6. dry with materialthe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified via flash chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-f5d596dc7c0a4f69bedebb07c35003a0
Source dataset
uspto-grants-2008_11
Patent number
US07446118B2

Reaction notes

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