Methyl Thioglycolate → HCID 86755648, compound

HRID 1871969Notes

Reaction equation

HRID 1871969 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH2:2][SH:3].[H-].[Na+].[CH:9]1[C:19]2[CH:18]=[CH:17][C:16]3[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=3[CH:14]([C:24]3[C:25](=[O:38])[NH:26][C:27](=[O:37])[N:28]([C:30]4[N:31]=[N:32][C:33](Cl)=[CH:34][CH:35]=4)[CH:29]=3)[C:13]=2[CH:12]=[CH:11][CH:10]=1>CN(C)C=O>[CH:20]1[C:16]2[CH:17]=[CH:18][C:19]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[CH:14]([C:24]3[C:25](=[O:38])[NH:26][C:27](=[O:37])[N:28]([C:30]4[N:31]=[N:32][C:33]([S:3][CH2:2][C:1]([O:5][CH3:6])=[O:4])=[CH:34][CH:35]=4)[CH:29]=3)[C:15]=2[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 16907Methyl ThioglycolateHCID 24758Sodium hydrideHCID 18689771HCID 18689771, compound

Product 1

HCID 86755648HCID 86755648, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Methyl thioglycolate (0.97 ml) was added dropwise to a stirred suspension of sodium hydride (0.434 g, 60% dispersion in oil) in dimethylformamide (30 ml). The mixture was stirred at room temperature for 1 hour. 13 ml of this solution was added to a solution of the product from step (i) (0.9 g) in dimethylformamide (20 ml). The mixture was stirred for 2 hours then quenched with aqueous arnmonium chloride and partitioned between ethyl acetate and water. The organic phase was dried (MgSO4) and evaporated. The residue was purified by chromatography eluting with 50% ethyl acetate in isohexane. Yield 1.0 g.

Workup

  1. stirringThe mixture was stirred for 2 hours
  2. customthen quenched with aqueous arnmonium chloride
  3. custompartitioned between ethyl acetate and water
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by chromatography
  7. washeluting with 50% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-30cd4a15e7b347f7a490192b81eeb8f1
Source dataset
uspto-grants-2000_08
Patent number
US06107297

Reaction notes

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