Thioglycolic Acid → HCID 54251855, compound

HRID 2260422Notes

Reaction equation

HRID 2260422 reaction equation
[SH:1][CH2:2][C:3]([OH:5])=[O:4].[C:6]1([S:12][C@@H:13]2[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]2O)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[C:6]1([S:12][C@@H:13]2[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]2[S:1][CH2:2][C:3]([OH:5])=[O:4])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 1133Thioglycolic AcidHCID 6422Trifluoroacetic acidHCID 11805926HCID 11805926, compound

Product 1

HCID 54251855HCID 54251855, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Mercaptoacetic acid (0.44 g, 0.0048 mole) was added to a cold solution of the compound of Example 6 (1.0 g, 0.0048 mole) in methylene chloride (5 ml) containing trifluoracetic acid (3.5 ml). The reaction mixture was stirred at room temperature for 20 hours. The reaction mixture was concentrated to an oil with a rotary evaporator. The residue was dissolved in diethyl ether (50 ml), washed three times with 20 ml of 5% sodium bicarbonate, followed by in hydrochloric acid (10 ml) and water (20 ml), dried over anhydrous magnesium sulfate, filtered and concentrated to a colorless oil with a rotary evaporator. The product was purified by silica gel chromatography. The structure was supported by NMR, infrared spectroscopy and elemental analysis.

Workup

  1. concentrationThe reaction mixture was concentrated to an oil with a rotary evaporator
  2. dissolutionThe residue was dissolved in diethyl ether (50 ml)
  3. washwashed three times with 20 ml of 5% sodium bicarbonate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to a colorless oil with a rotary evaporator
  7. customThe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-e51ae04f5aee42afae5abcf78ad4105b
Source dataset
uspto-grants-1995_12
Patent number
US05476944

Reaction notes

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