Ethanol → HCID 53768583, compound

HRID 903447Notes

Reaction equation

HRID 903447 reaction equation
[H-].[Na+].C(O)(=[S:10])C1C=CC=CC=1.[CH2:12]([OH:14])[CH3:13].[Br:15][C:16]1[CH:36]=[CH:35][C:19]([C:20]([CH:22](Br)[CH2:23][C:24]([N:26]2[CH2:33][CH2:32][CH2:31][C@H:27]2[C:28]([OH:30])=[O:29])=O)=[O:21])=[CH:18][CH:17]=1.C(OCC)(=O)C.[CH3:43][CH2:44][CH2:45][CH2:46][CH2:47]C.C(O)(=O)C>>[Br:15][C:16]1[CH:36]=[CH:35][C:19]([C:20]([CH:22]([C:12](=[O:14])[C:13]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH2:23][C:24]([N:26]2[CH2:33][CH2:32][CH2:31][C@H:27]2[C:28]([OH:30])=[O:29])=[S:10])=[O:21])=[CH:18][CH:17]=1

Participants

6

Reactant 5

HCID 702EthanolHCID 24758Sodium hydrideHCID 21901998Ethyl acetate hexane acetic acidHCID 539233931-[3-(4-Bromobenzoyl)-3-bromopropionyl]-L-prolineHCID 178526132HCID 178526132, compound

Product 1

HCID 53768583HCID 53768583, compound

Procedure

To 440 mg. of sodium hydride in oil dispersion is added a solution of 1.60 g. of thiobenzoic acid in 25 ml. of ethanol. The mixture is stirred for 30 minutes and then 4.33 g. of 1-[3-(4-bromobenzoyl)-3-bromopropionyl]-L-proline (Example 37) is added and the mixture is stirred at room temperature for 18 hours, the solvent is removed in vacuo and the residue is partitioned between dichloromethane and water. The organic layer is washed with water, then sodium chloride solution, dried over magnesium sulfate and evaporated to dryness in vacuo leaving a peach colored glass. A 2.8 g. portion of this glass is dissolved in ethyl acetate-hexane-acetic acid (75:25:2) and placed on a 1"×15" column of silica gel. The column is eluted with the same solvent system (100 ml. hold back volume) taking 50 ml. cuts. The desired product is recovered in cut number 2 as a glass.

Workup

  1. stirringthe mixture is stirred at room temperature for 18 hours
  2. customthe solvent is removed in vacuo
  3. customthe residue is partitioned between dichloromethane and water
  4. washThe organic layer is washed with water
  5. dry with materialsodium chloride solution, dried over magnesium sulfate
  6. customevaporated to dryness in vacuo
  7. customleaving a peach colored glass
  8. washThe column is eluted with the same solvent system (100 ml. hold back volume)
  9. customThe desired product is recovered in cut number 2 as a glass

Sources & evidence

ORD record
ord-e1fc875b80ed4f8e80208f478136e812
Source dataset
uspto-grants-1980_10
Patent number
US04226775

Reaction notes

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