Potassium ethanethioate → 1-[3-Acetylthio-3-(4-bromobenzoyl)propionyl]-L-proline

HRID 903446Notes

Reaction equation

HRID 903446 reaction equation
[C:1]([O-:4])(=[S:3])[CH3:2].[K+].[Br:6][C:7]1[CH:27]=[CH:26][C:10]([C:11]([CH:13](Br)[CH2:14][C:15]([N:17]2[CH2:24][CH2:23][CH2:22][C@H:18]2[C:19]([OH:21])=[O:20])=[O:16])=[O:12])=[CH:9][CH:8]=1>C(O)C>[C:1]([S:3][CH:13]([C:11](=[O:12])[C:10]1[CH:26]=[CH:27][C:7]([Br:6])=[CH:8][CH:9]=1)[CH2:14][C:15]([N:17]1[CH2:24][CH2:23][CH2:22][C@H:18]1[C:19]([OH:21])=[O:20])=[O:16])(=[O:4])[CH3:2]

Participants

4

Reactant 2

HCID 23670855Potassium ethanethioateHCID 539233931-[3-(4-Bromobenzoyl)-3-bromopropionyl]-L-proline

Product 1

HCID 541484881-[3-Acetylthio-3-(4-bromobenzoyl)propionyl]-L-proline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred suspension of 469 mg. of potassium thioacetate in 10 ml. of ethanol is added 1.76 g. of 1-[3-(4-bromobenzoyl)-3-bromopropionyl]-L-proline (Example 37). The mixture is stirred at room temperature for 18 hours, filtered and the filtrate evaporated to dryness. The residue is dissolved in dichloromethane, washed with water and saturated sodium chloride solution, dried over magnesium sulfate and evaporated to dryness in vacuo giving the desired product as 1.68 g. of a white glass.

Workup

  1. additionTo a stirred suspension of 469 mg
  2. filtrationfiltered
  3. customthe filtrate evaporated to dryness
  4. dissolutionThe residue is dissolved in dichloromethane
  5. washwashed with water and saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-a6470c9ac0c0424486841b4959d65c35
Source dataset
uspto-grants-1980_10
Patent number
US04226775

Reaction notes

Loading…