Methyl Thioglycolate → HCID 15289735, compound

HRID 37635Notes

Reaction equation

HRID 37635 reaction equation
C[O-].[Na+].[C:4]([O:8][CH3:9])(=[O:7])[CH2:5][SH:6].[CH3:10][C:11]([C:14]1[CH:15]=[C:16]([CH2:24][CH2:25][C@H:26]2[CH2:30][CH2:29][CH2:28][C@H:27]2C2C=C(C)C=CC=2S([O-])(=O)=O)[CH:17]=[C:18]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:19]=1)([CH3:13])[CH3:12]>CO>[CH3:13][C:11]([C:14]1[CH:15]=[C:16]([CH2:24][CH2:25][C@@H:26]2[CH2:27][CH2:28][CH2:29][C@H:30]2[S:6][CH2:5][C:4]([O:8][CH3:9])=[O:7])[CH:17]=[C:18]([C:20]([CH3:21])([CH3:22])[CH3:23])[CH:19]=1)([CH3:10])[CH3:12]

Participants

5

Reactant 3

HCID 16907Methyl ThioglycolateHCID 10942334Sodium MethoxideHCID 86748704HCID 86748704, compound

Product 1

HCID 15289735HCID 15289735, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of sodium methoxide (prepared from 38 mg of sodium) in 10 ml of methanol is added 174 mg (1.64 mmoles) of methyl thioglycolate. After stirring for a few minutes, a solution of 500 mg (1.09 mmoles) of the title product of Example 38 in 5 ml of methanol is added, and stirring is continued until TLC indicates the reaction is complete. The mixture is then partitioned between diethyl ether and water, the organic layer dried over sodium sulfate, filtered, and evaporated. Chromatography of the residue over silica gel using mixtures of ethyl acetate and hexane as eluents gives the title compound.

Workup

  1. stirringstirring
  2. customThe mixture is then partitioned between diethyl ether and water
  3. dry with materialthe organic layer dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-0811074a932244cf8a18ca09342b9fd5
Source dataset
uspto-grants-1995_05
Patent number
US05420343

Reaction notes

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