Thiophenol → HCID 66918859, compound

HRID 1367456Notes

Reaction equation

HRID 1367456 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:10]([O:12][C:13]([C@@H:15]1[CH2:19][C@H:18](OS(C)(=O)=O)[CH2:17][C@H:16]1[C:25]([N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)=[O:26])=[O:14])[CH3:11]>C1COCC1>[CH2:10]([O:12][C:13]([C@@H:15]1[CH2:19][C@@H:18]([S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:17][C@H:16]1[C:25]([N:27]1[CH2:28][CH2:29][O:30][CH2:31][CH2:32]1)=[O:26])=[O:14])[CH3:11]

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 24758Sodium hydrideHCID 86649015HCID 86649015, compound

Product 1

HCID 66918859HCID 66918859, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of the thiophenol (0.41 mmol) in THF (4 ml) was added NaH (55% in oil, 0.41 mmol) at 22° C. and stirring was continued until gas evolution ceased. To the mixture was added a solution of (1R,2R,4R)-4-methanesulfonyloxy-2-(morpholine-4-carbonyl)-cyclopentanecarboxylic acid ethyl ester (0.28 mmol) in THF (4 ml) and stirring was continued at 50° C. until completion of the reaction. The mixture was partitioned between ethyl acetate and water, the organic layer was dried, evaporated and the residue chromatographed on silica using mixtures of cyclohexane and ethyl acetate to give the title compound as pale yellow oil. MS: 364.5 (M+H)+.

Workup

  1. stirringstirring
  2. customwas continued at 50° C. until completion of the reaction
  3. customThe mixture was partitioned between ethyl acetate and water
  4. customthe organic layer was dried
  5. customevaporated
  6. customthe residue chromatographed on silica using mixtures of cyclohexane and ethyl acetate

Sources & evidence

ORD record
ord-adbe35b754aa4efb9c3b3f935d0ff495
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

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