Thioglycolic Acid → HCID 54237278, compound

HRID 903467Notes

Reaction equation

HRID 903467 reaction equation
C(S[CH:5]([CH2:16][C:17](=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=[O:11])=[O:7])(=O)C.C(Cl)(Cl)(Cl)Cl.[SH:30][CH2:31][C:32]([OH:34])=[O:33]>C(O)C>[C:17]([CH2:16][CH:5]([S:30][CH2:31][C:32]([OH:34])=[O:33])[C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=[O:11])=[O:7])(=[O:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 1133Thioglycolic AcidHCID 5943Carbon Tetrachloride2×HCID 54557715HCID 54557715, compound

Product 1

HCID 54237278HCID 54237278, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 0.90 g. of 1-(3-benzoylacryloyl)-L-proline (prepared as described in Example 8) in 30 ml. of carbontetrachloride is added 0.28 ml. of mercaptoacetic acid. An additional 30 ml. of carbontetrachloride is added and the mixture stirred 3 days. The solvent is removed under vacuum. Carbontetrachloride (30 ml.) and 0.78 ml. of mercaptoacetic acid is added and the mixture stirred for 3 days. The solvent is removed and the residue chromatographed on a silica gel column with dichloromethane-methanol-acetic acid (90:10:2) as solvent. Fractions showing one spot by thin layer chromatography are combined to give 1.3 g. of clear gum. Placing the gum under high vacuum over night gives the product of the example as a glass, [α]D23° -31°±2(c, 0.534 ethanol).

Workup

  1. additionTo a suspension of 0.90 g
  2. customThe solvent is removed under vacuum
  3. additionof mercaptoacetic acid is added
  4. stirringthe mixture stirred for 3 days
  5. customThe solvent is removed
  6. customthe residue chromatographed on a silica gel column with dichloromethane-methanol-acetic acid (90:10:2) as solvent
  7. customto give 1.3 g

Sources & evidence

ORD record
ord-839cdfe4da764ffca802b634fe630d35
Source dataset
uspto-grants-1980_10
Patent number
US04226775

Reaction notes

Loading…