Acetonitrile → 1-[3-(Benzoylthio)-3-(benzo[b]thien-3-ylcarbonyl)propionyl]-L-proline

HRID 66510Notes

Reaction equation

HRID 66510 reaction equation
Br[CH:2]([C:14]([C:16]1[C:17]2[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=2[S:19][CH:20]=1)=[O:15])[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:31]([OH:39])(=[S:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(O)(=O)C>[C:31]([S:38][CH:2]([C:14]([C:16]1[C:17]2[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=2[S:19][CH:20]=1)=[O:15])[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:39])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 6342Acetonitrile2×HCID 10942334Sodium MethoxideHCID 536867021-[3-bromo-3-(benzo[b]thien-3-ylcarbonyl)propionyl]-L-prolineHCID 178526132HCID 178526132, compound

Product 1

HCID 536406471-[3-(Benzoylthio)-3-(benzo[b]thien-3-ylcarbonyl)propionyl]-L-proline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

As for Example 21, 1-[3-bromo-3-(benzo[b]thien-3-ylcarbonyl)propionyl]-L-proline (0.01 mole) in 25 ml. of acetonitrile is added to a mixture of 0.01 mole of sodium methoxide and 0.015 mole of thiobenzoic acid in 25 ml. of acetonitrile. The mixture is stirred at room temperature for 16 hours, one ml. of acetic acid is added and the solvent is evaporated in vacuo. The residue is partitioned between dichloromethane and water containing acetic acid. The organic layer is separated, washed with water and dried over magnesium sulfate. The solvent is removed in vacuo to give the product of the Example as a yellow glass.

Workup

  1. customthe solvent is evaporated in vacuo
  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 is removed in vacuo
  8. customto give the product of the Example as a yellow glass

Sources & evidence

ORD record
ord-4ebb3827a23c42ca861cb51bafa4df8f
Source dataset
uspto-grants-1982_08
Patent number
US04342690

Reaction notes

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