Tetrahydrofuran → HCID 86678224, compound

HRID 2362307Notes

Reaction equation

HRID 2362307 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C@@H:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[N:9]2[C:19](=[O:32])[N:20]([CH2:22][CH2:23][CH2:24][S:25]([CH2:28][CH2:29][CH2:30][OH:31])(=[O:27])=[O:26])[N:21]=[C:8]2[N:7]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:42])([F:41])[F:40])[CH:34]=2)[C:6]=1[CH3:43])=[O:4].[H-].[Na+].[C:46]1(C)[C:47]([S:52](Cl)(=[O:54])=[O:53])=[CH:48][CH:49]=[CH:50][CH:51]=1.[CH2:57]1COCC1>>[CH3:1][O:2][C:3]([C:5]1[C@@H:10]([C:11]2[CH:12]=[CH:13][C:14]([C:17]#[N:18])=[CH:15][CH:16]=2)[N:9]2[C:19](=[O:32])[N:20]([CH2:22][CH2:23][CH2:24][S:25]([CH2:28][CH2:29][CH2:30][O:31][S:52]([C:47]3[CH:46]=[CH:51][C:50]([CH3:57])=[CH:49][CH:48]=3)(=[O:53])=[O:54])(=[O:26])=[O:27])[N:21]=[C:8]2[N:7]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:40])([F:42])[F:41])[CH:34]=2)[C:6]=1[CH3:43])=[O:4]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8623o-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 71293508HCID 71293508, compound

Product 1

HCID 86678224HCID 86678224, compound

Procedure

Intermediate 28 (470 mg, 0.76 mmol) was dissolved in THF (5 ml), and then sodium hydride (48 mg, 1.2 mmol) was added under an atmosphere of N2. The reaction mixture was stirred at RT for 10 mins, then toluenesulfonyl chloride (191 mg, 1 mmol) was added and stirring was continued for 16 hours. The reaction mixture was partitioned between EtOAc and water. The organic layer was separated, washed with brine, dried (Na2SO4) and evaporated in vacuo. The resulting residue was purified by silica gel chromatography eluing with a gradient of 50-80% EtOAc in cyclohexane to give the title compound as a pale yellow glass (132 mg).

Workup

  1. stirringstirring
  2. waitwas continued for 16 hours
  3. customThe reaction mixture was partitioned between EtOAc and water
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo
  8. customThe resulting residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-d42d1a58d2d2445da9eda0344bccbe10
Source dataset
uspto-grants-2014_04
Patent number
US08691826B2

Reaction notes

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