Hydrochloric Acid → O-(3-Mercaptopropanoyl)glycolic Acid
Reaction equation
C([S:4][CH2:5][CH2:6][C:7]([O:9][C:10](=[O:13])[CH2:11][OH:12])=[O:8])(=O)C.[OH-].[NH4+].Cl>O>[SH:4][CH2:5][CH2:6][C:7]([O:9][C:10](=[O:13])[CH2:11][OH:12])=[O:8]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
O-(3-acetylthiopropanoyl)glycolic acid from Example 1 (1.3 g), under a blanket of argon is treated for fifteen minutes with a cold solution of 7 ml of water and 7 ml of concentrated ammonium hydroxide. This is chilled, acidified with concentrated hydrochloric acid and extracted into ethyl acetate, yield: 1.2 g. This product O-(3-mercaptopropanoyl)glycolic acid is chromatographed on DEAE Sephadex A25 (Polidextrane anion exchange resin) with a linear gradient of ammonium bicarbonate. The desired fractions (45-70; U.V. peak at 254 nm.) are pooled, concentrated and lyophilized. This ammonium salt of O-(3-mercaptopropanoyl)glycolic acid is converted to the free acid by treatment with Dowex 50WX2 cation exchange resin, yield 320 mg. The O-(3-mercaptopropanoyl)glycolic acid is converted to the dicyclohexylamine salt by dissolving in ether and precipitating by the addition of dicyclohexylamine, m.p. 143°-144°.
Workup
- temperatureThis is chilled
- extractionextracted into ethyl acetate, yield: 1.2 g
- customThis product O-(3-mercaptopropanoyl)glycolic acid is chromatographed on DEAE Sephadex A25 (Polidextrane anion exchange resin) with a linear gradient of ammonium bicarbonate
- concentrationconcentrated
- dissolutionby dissolving in ether
- customprecipitating by the addition of dicyclohexylamine, m.p. 143°-144°
Sources & evidence
- ORD record
- ord-98ae735ad312429d91fe96066d413144
- Source dataset
- uspto-grants-1986_09
- Patent number
- US04611002
Reaction notes
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