Tetrahydrofuran → HCID 86678224, compound

HRID 570880Notes

Reaction equation

HRID 570880 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 Bluing 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 Bluing with a gradient of 50-80% EtOAc in cyclohexane

Sources & evidence

ORD record
ord-4198cc1b4bbf4947a74af796854f6bdc
Source dataset
uspto-grants-2015_05
Patent number
US09023855B2

Reaction notes

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