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

HRID 64911노트

반응식

HRID 64911 반응식
[C:1]([S:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8])(=[O:3])[CH3:2].[C:10](O)(=[O:13])[CH2:11][OH:12].C(N(CC)CC)C>O1CCCC1>[C:1]([S:4][CH2:5][CH2:6][C:7]([O:9][C:11](=[O:12])[CH2:10][OH:13])=[O:8])(=[O:3])[CH3:2]

참가 물질

5

반응물 3

HCID 757Glycolic AcidHCID 8471TriethylamineHCID 2627193-(Acetylthio)propionic Acid

생성물 1

HCID 86737402O-(3-Acetylthiopropanoyl)glycolic Acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

3-(Acetylthio)propanoic acid (2.96 g) and 1,1'-carboxyldiimidazole (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 dry 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 1N 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.

후처리

  1. waitAfter twenty minutes
  2. customThe tetrahydrofuran is removed in vacuo
  3. washwashed with 1N 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

출처 및 근거

ORD 기록
ord-40ea0f83f3e74390bba517a8ce795050
출처 데이터셋
uspto-grants-1986_09
특허 번호
US04611002

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