Glycolic Acid → O-(3-Acetylthiopropanoyl)glycolic Acid

HRID 1733411Notes

Reaction equation

HRID 1733411 reaction equation
[C:1]([S:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8])(=[O:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[C:22](O)(=[O:25])[CH2:23][OH:24]>O1CCCC1.C(N(CC)CC)C>[C:1]([S:4][CH2:5][CH2:6][C:7]([O:9][C:23](=[O:24])[CH2:22][OH:25])=[O:8])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 757Glycolic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 2627193-(Acetylthio)propionic Acid

Product 1

HCID 86737402O-(3-Acetylthiopropanoyl)glycolic Acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

3-(Acetylthio)propanoic acid (2.96 g.) and 1,1'-carbonyldiimidazole (3.24 g.) are dissolved in 20 ml. of dry tetrahydrofuran with stirring at room temperature. After twenty minutes, a solution of glycolic acid (1.52 g.) and 2.80 ml. of triethylamine in 15 ml. of tetrahydrofuran are added. The reaction mixture is stored overnight at room temperature. The tetrahydrofuran is removed in vacuo, the crude residue taken up into ethyl acetate, washed with 1 N hydrochloric acid and three times with water, dried over magnesium sulfate and the O-(3-acetylthiopropanoyl)glycolic acid is concentrated to dryness in vacuo, yield 3.9 g. This is dissolved in ether and dicyclohexylamine is added. The dicyclohexylamine salt precipitates, yield 2.85 g., m.p. 150°-157°. The salt is converted to the free acid by adding to ethyl acetate and adding 10% potassium bisulfate solution, yield 1.5 g.

Workup

  1. waitAfter twenty minutes
  2. customThe tetrahydrofuran is removed in vacuo
  3. washwashed with 1 N hydrochloric acid and three times with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationthe O-(3-acetylthiopropanoyl)glycolic acid is concentrated to dryness in vacuo, yield 3.9 g
  6. dissolutionThis is dissolved in ether
  7. additiondicyclohexylamine is added
  8. customThe dicyclohexylamine salt precipitates
  9. additionby adding to ethyl acetate
  10. additionadding 10% potassium bisulfate solution, yield 1.5 g

Sources & evidence

ORD record
ord-1a45d2d515ed4845b294f67b6b17338c
Source dataset
uspto-grants-1980_12
Patent number
US04242265

Reaction notes

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