Acetonitrile → 1-[3-(Benzoylthio)-3-(2-thenoyl)propionyl]-L-proline

HRID 66486Notes

Reaction equation

HRID 66486 reaction equation
Br[CH:2]([C:14](=[O:20])[C:15]1[S:19][CH:18]=[CH:17][CH:16]=1)[CH2:3][C:4]([N:6]1[CH2:13][CH2:12][CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5].C(#N)C.C[O-].[Na+].[C:27]([OH:35])(=[S:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(O)(=O)C>[C:27]([S:34][CH:2]([C:14](=[O:20])[C:15]1[S:19][CH:18]=[CH:17][CH:16]=1)[CH2:3][C:4]([N:6]1[CH2:13][CH2:12][CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5])(=[O:35])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 10942334Sodium MethoxideHCID 127660951-[3-bromo-3-(2-thenoyl)propionyl]-L-prolineHCID 178526132HCID 178526132, compound

Product 1

HCID 542407671-[3-(Benzoylthio)-3-(2-thenoyl)propionyl]-L-proline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

As for Example 1, 1-[3-bromo-3-(2-thenoyl)propionyl]-L-proline (0.0085 mole) in 25 ml. of acetonitrile is added to a mixture of 0.015 mole of sodium methoxide and 0.015 mole of thiobenzoic acid in 25 ml. of acetontrile. The mixture is stirred at room temperature for 16 hours, one ml. of acetic acid is added and the solvent removed under reduced pressure. The residue is partitioned between dichloromethane and water containing acetic acid. The organic layer is separated, washed with water, dried over magnesium sulfate and the solvent removed under reduced pressure to give the product of the Example as a pale yellow glass.

Workup

  1. customthe solvent removed under reduced pressure
  2. customThe residue is partitioned between dichloromethane and water
  3. additioncontaining acetic acid
  4. customThe organic layer is separated
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent removed under reduced pressure
  8. customto give the product of the Example as a pale yellow glass

Sources & evidence

ORD record
ord-59e3c064912c4a6893527dce2c50568f
Source dataset
uspto-grants-1982_08
Patent number
US04342689

Reaction notes

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