Glycolic Acid → HCID 88674943, compound

HRID 1733413Notes

Reaction equation

HRID 1733413 reaction equation
[C:1]([S:4][CH2:5][CH:6]([CH3:10])[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[C:23](O)(=[O:26])[CH2:24][OH:25].N1C=CN=C1>O1CCCC1.C(N(CC)CC)C>[C:1]([S:4][CH2:5][CH:6]([CH3:10])[C:7]([O:9][C:24](=[O:25])[CH2:23][OH:26])=[O:8])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 757Glycolic Acid2×HCID 795ImidazoleHCID 682631,1'-CarbonyldiimidazoleHCID 1180733-(Acetylthio)-2-methylpropanoic acid

Product 1

HCID 88674943HCID 88674943, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

3-Acetylthio-2-methylpropanoic acid (6.48 g.) is taken into 40 ml. of dry tetrahydrofuran. To this 1,1'-carbonyldiimidazole (0.48 g.) is added and stirred for 30 minutes at room temperature. Glycolic acid (6.08 g.) and 11.2 ml. of triethylamine in 60 ml. of dry tetrahydrofuran are added. After several minutes, the imidazole salt of glycolic acid begins to come out of solution. The reaction is permitted to run overnight at room temperature. The crystalline salt is filtered and the filtrate concentrated to dryness in vacuo. The residue is taken up into ethyl acetate, washed with 1 N hydrochloric acid and three times with water, dried over magnesium sulfate and concentrated to dryness in vacuo. This product is converted to its dicyclohexylamine salt by dissolving in ether/hexane and precipitating by the addition of dicyclohexylamine. The salt is recrystallized from ether, m.p. 120°-122°. This salt is then converted to the free acid, O-[3-(acetylthio)-2-methylpropanoyl]glycolic acid, by adding to ethyl acetate, adding 10% potassium bisulfate solution, then crystallizing from ethyl/hexane, yield 2.96 g., m.p. 50°-51°.

Workup

  1. waitAfter several minutes
  2. waitto run overnight at room temperature
  3. filtrationThe crystalline salt is filtered
  4. concentrationthe filtrate concentrated to dryness in vacuo
  5. washwashed with 1 N hydrochloric acid and three times with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated to dryness in vacuo
  8. dissolutionby dissolving in ether/hexane
  9. customprecipitating by the addition of dicyclohexylamine
  10. customThe salt is recrystallized from ether, m.p. 120°-122°
  11. additionby adding to ethyl acetate
  12. additionadding 10% potassium bisulfate solution
  13. customcrystallizing from ethyl/hexane, yield 2.96 g

Sources & evidence

ORD record
ord-f4da33e11294482b980d875f10c090d1
Source dataset
uspto-grants-1980_12
Patent number
US04242265

Reaction notes

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